Production process of 2-(4-chlorophenoxy)propylhydroxylamine

Abstract

The present invention belongs to the field of organic synthesis, and particularly relates to a production process of 2-(4-chlorophenoxy)propylhydroxylamine, which comprises the following steps: S1. Synthesis of methyl 2-(4-chlorophenoxy)propionate: Add DMF, 4-chlorophenol, and potassium carbonate to a substitution reaction kettle, heat to 50-70 °C, and keep the temperature for reaction for 1-2 h. After the heat preservation is completed, add methyl 2-chloropropionate and potassium iodide to the substitution reaction kettle, heat to 60-80 °C, and keep the temperature for reaction for 1-3 h. After the reaction is completed, perform post-treatment to obtain methyl 2-(4-chlorophenoxy)propionate; S2. Synthesis of 2-(4-chlorophenoxy)propanol; S3. Synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate; S4. Synthesis of 2-(4-chlorophenoxy)propyl acetate oxime; S5. Synthesis of 2-(4-chlorophenoxy)propylhydroxylamine. The beneficial effects of the present invention are as follows: The present invention adopts a new synthetic route to prepare 2-(4-chlorophenoxy)propylhydroxylamine. The reaction conditions are mild, the highest reaction temperature does not exceed 80 °C, the reaction yield is relatively high, and the overall yield is also relatively high, which is suitable for large-scale production.

Description

Technical Field

[0001] The present invention belongs to the field of organic synthesis, and particularly relates to a production process of 2-(4-chlorophenoxy)propylhydroxylamine. Background Art

[0002] 2-(4-Chlorophenoxy)propylhydroxylamine is an important organic intermediate, with the English name 2-(4-chlorophenoxy)propyl)hydroxylamine. In the prior art, the synthesis of 2-(4-chlorophenoxy)propylhydroxylamine generally uses groups such as ketoxime, ketoxime derivatives, N-hydroxyphthalimide and its derivatives for protection, and then deprotection is carried out to obtain it. This method has detailed synthesis reports in journals such as Tetrahedron Letters, 1988, Vol. 29, 701-704 and J. Org. Chem. 2005, 70, 6303-6312; however, this method has some disadvantages: the reaction raw materials involved in the whole synthesis process are expensive, the reaction yield is low, and compounds such as hydrazines must be used in the hydrolysis process, and the reaction safety is poor. Summary of the Invention

[0003] In order to solve the above problems, the present invention provides a production process of 2-(4-chlorophenoxy)propylhydroxylamine.

[0004] The present invention provides the following technical solutions:

[0005] A production process of 2-(4-chlorophenoxy)propylhydroxylamine, comprising the following steps:

[0006] S1. Synthesis of methyl 2-(4-chlorophenoxy)propionate

[0007] Add DMF, 4-chlorophenol, and potassium carbonate to the substitution reaction kettle, heat to 50-70°C, keep the temperature for reaction for 1-2 h. After the heat preservation ends, add methyl 2-chloropropionate and potassium iodide to the substitution reaction kettle, heat to 60-80°C, keep the temperature for reaction for 1-3 h. After the reaction ends, perform post-treatment to obtain methyl 2-(4-chlorophenoxy)propionate;

[0008] S2. Synthesis of 2-(4-chlorophenoxy)propanol

[0009] Add methanol and methyl 2-(4-chlorophenoxy)propionate to the reduction reaction kettle, keep the temperature in the reaction kettle at 25-30°C, displace with nitrogen, add sodium borohydride, control the reaction temperature at 45-50°C, keep the temperature for reaction. After the reaction ends, perform post-treatment to obtain 2-(4-chlorophenoxy)propanol;

[0010] S3. Synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate

[0011] Prepare a toluenesulfonyl chloride / dichloromethane mixed solution for use. Add a catalyst, 2-(4-chlorophenoxy)propanol, and triethylamine to the sulfonic acid esterification reaction kettle. Cool down to 5 - 10 °C, and slowly add the toluenesulfonyl chloride / dichloromethane solution while controlling the reaction temperature below 30 °C. After the addition is complete, maintain the reaction temperature at 25 - 30 °C and stir for the reaction. After the reaction ends, perform post-treatment to obtain 2-(4-chlorophenoxy)propyl p-toluenesulfonate;

[0012] S4. Add DMF, hydroxylamine hydrochloride, sodium hydroxide, methyl acetate, and 2-(4-chlorophenoxy)propyl p-toluenesulfonate to the oxime etherification reaction kettle. Stir at 20 - 30 °C for 1 - 3 h, then heat and keep the reaction at a constant temperature. After the reaction ends, perform post-treatment to obtain ;

[0013] S5. Synthesis of 2-(4-chlorophenoxy)propylhydroxylamine

[0014] Add to the acidification reaction kettle, add water and hydrochloric acid, heat and keep the reaction at a constant temperature, and perform post-treatment to obtain 2-(4-chlorophenoxy)propylhydroxylamine.

[0015] Preferably, the catalyst in S3 is 4-dimethylaminopyridine.

[0016] Preferably, the mass ratio of 4-dimethylaminopyridine to 2-(4-chlorophenoxy)propanol is (0.05 - 0.1):1.

[0017] Preferably, the catalyst in S3 is 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine.

[0018] Preferably, the mass ratio of 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine to 2-(4-chlorophenoxy)propanol is (0.01 - 0.1):1.

[0019] Preferably, the mass ratio of 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine to 2-(4-chlorophenoxy)propanol is 0.05:1.

[0020] Preferably, the holding time of the reaction at a constant temperature in step S2 is 2 - 4 h.

[0021] Preferably, the stirring time of the reaction in step S3 is 2 - 4 h.

[0022] Preferably, in the step S4, the heating temperature is 60-80°C, and the holding reaction time is 8-10h.

[0023] Preferably, in the step S5, the heating temperature is 50-70°C, and the holding reaction time is 8-12h.

[0024] The beneficial effects of the present invention are as follows:

[0025] 1. The present invention uses a new synthetic route to prepare 2-(4-chlorophenoxy)propylhydroxylamine. The reaction conditions are mild, the highest reaction temperature does not exceed 80°C, the reaction yields of each step are relatively high, and the overall yield is also relatively high, which is suitable for large-scale production.

[0026] 2. In the synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate in step S3 of the present invention, two catalysts are used, both of which produce good catalytic effects. Especially 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine, with less dosage and shorter reaction time, and at the same time can achieve higher yields. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 Flow chart of the process of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0028] The following specifically describes the present invention with reference to specific embodiments.

[0029] Unless otherwise specified, the reagents used in the present invention are all commercially available.

[0030] The reaction equation of the present invention is as follows:

[0031] S1. Synthesis of methyl 2-(4-chlorophenoxy)propionate

[0032]

[0033] S2. Synthesis of 2-(4-chlorophenoxy)propanol

[0034]

[0035]

[0036] S3. Synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate

[0037]

[0038] S4.

[0039] S5. Synthesis of 2-(4-chlorophenoxy)propylhydroxylamine

[0040]

[0041] Example 1

[0042] A synthesis process of 2-(4-chlorophenoxy)propylhydroxylamine, comprising the following steps:

[0043] S1. Synthesis of methyl 2-(4-chlorophenoxy)propionate

[0044] 1800 g of DMF was vacuum drawn into a 5 L substitution reactor. 500 g of 4-chlorophenol and 800 g of potassium carbonate were added to the feeding bin, and the temperature was raised to 60 °C by heating for 1.5 - 2 h, and the reaction was carried out under insulation for 1 h. After the insulation was completed, 550 g of methyl 2-chloropropionate was added to the substitution reactor, 50 g of potassium iodide was added to the feeding bin, and the temperature was raised to 80 °C by heating for 1 - 1.5 h, and the reaction was carried out under insulation for 2 h. The conversion rate was 99% (calculated based on 4-chlorophenol). Filtration was carried out. The filter cake of 700 - 800 g was washed with 500 g of dichloromethane, and neutralized with a certain amount of hydrochloric acid to pH = 7. Potassium chloride was used as a by-product. The washing solvent was sent to a distillation kettle for atmospheric distillation, and dichloromethane was recovered and recycled for the washing process. The remaining DMF after distillation (vacuum distillation above 0.098 Mpa, about 60 °C) was recycled for the reaction. The filtrate was heated in a distillation kettle and subjected to vacuum distillation (vacuum distillation above 0.098 Mpa, about 60 °C), and the condensate was collected by one-stage water cooling + one-stage freezing condensation (condenser configuration, condensing medium, condensing temperature -10 °C) and recycled for the reaction process. After the vacuum distillation was completed, 500 g of water was added, stirred and washed, and allowed to stand for separation. The upper oil phase was used as the intermediate methyl 2-(4-chlorophenoxy)propionate for the next reaction; the lower aqueous phase was placed in an extraction kettle, 500 g of dichloromethane was added, stirred for extraction, and allowed to stand for separation. The aqueous phase was evaporated and crystallized to recover potassium iodide for recycling in the reaction, and the oil phase was subjected to atmospheric distillation to recover dichloromethane for recycling in the extraction process. The remaining material after distillation was used as the intermediate methyl 2-(4-chlorophenoxy)propionate (total 805.5 g, yield 96.8%) for the next reaction.

[0045] S2. Synthesis of 2-(4-chlorophenoxy)propanol

[0046] Add 1000 g of methanol and 800 g of methyl 2-(4-chlorophenoxy)propionate to a 5 L reduction reactor, keep the temperature in the reactor at 25 - 30 °C, and displace with nitrogen (nitrogen pressure 0.1 MPa) for 15 min. Add 150 g of sodium borohydride to the reactor through the feeding bin, control the reaction temperature at 45 °C, and keep the reaction for 3 h under insulation. After the reaction is completed, distill at atmospheric pressure, and collect the condensate methanol through first-stage water cooling + first-stage freezing condensation (-10 °C) for recycling in the reduction reaction process. After the distillation is completed, add a certain amount of 32% hydrochloric acid to the distillation kettle, stir and neutralize, distill at atmospheric pressure, and collect the condensate as by-product methanol through first-stage water cooling + first-stage freezing condensation; add 800 g of water to the reactor, filter by suction, and the filter cake is boric acid (water crystal, as a by-product). After the filtrate is collected and allowed to stand for stratification, the upper aqueous phase is extracted with 100 g of dichloromethane, and the aqueous phase is sent to the sewage treatment station as wastewater. The dichloromethane phase is distilled to recover the product and combined with the lower organic phase to obtain 2-(4-chlorophenoxy)propanol (653.1 g, yield 93.8%).

[0047] S3. Synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate

[0048] Add 500 g of p-toluenesulfonyl chloride and 1500 g of dichloromethane to the sulfonic acid esterification reactor, stir for 1 h for standby. Add 50 g of the catalyst 4-dimethylaminopyridine to the reactor, add a certain amount of 500 g of 2-(4-chlorophenoxy)propanol and 400 g of triethylamine, cool down to 5 - 10 °C with ice brine, and slowly add the p-toluenesulfonyl chloride and dichloromethane solution, controlling the reaction temperature below 30 °C. After the feeding is completed in 3 - 4 h, keep the reaction temperature at 25 - 30 °C and stir for 4 h. After the reaction is completed, add 800 g of water to the reactor, stir and wash, allow to stand for stratification, add alkali to the upper aqueous phase until pH = 9, recover triethylamine and the catalyst for reuse, and send the water to the sewage treatment station for treatment; discharge the lower organic phase into the distillation kettle, distill at atmospheric pressure, and recover dichloromethane through first-stage water cooling + first-stage freezing condensation (-10 °C) for recycling in the reaction. After the distillation is completed, obtain the product 2-(4-chlorophenoxy)propyl p-toluenesulfonate (815.3 g, yield 89.3%). Take 750 g of 2-(4-chlorophenoxy)propyl p-toluenesulfonate, add 1000 g of DMF, stir evenly, and send it to the next reaction.

[0049] S4. Add 1200 g of DMF into the oxime etherification reactor, add 225 g of hydroxylamine hydrochloride, 250 g of sodium hydroxide flakes, and 320 g of methyl acetate into the feeding bin. Add the DMF solution of 2-(4-chlorophenoxy)propyl p-toluenesulfonate and stir at room temperature for 2 h. After the heat preservation is completed, heat for 1.5 - 2 h to 80 °C and keep the reaction at this temperature for 8 - 10 h. After the reaction is completed, filter the material by vacuum filtration. The filter cake is washed with 500 g of dichloromethane (splashing washing) and then sent to the salt recovery process. After the filtrate is collected by the distillation kettle, it is mixed with the dichloromethane washing solution, and dichloromethane is recovered by atmospheric distillation, first-stage water cooling + first-stage freezing condensation (condenser configuration, condensing medium, condensing temperature -10 °C) and recycled for the reaction. The remaining material after distillation is sent to the next reaction as the product (515.3 g, yield 96.1%).

[0050] S5. Synthesis of 2-(4-chlorophenoxy)propylhydroxylamine

[0051] Add 500 g of into the acidification reactor, add 500 g of water and 200 g of 30% hydrochloric acid, heat for 2 h to the material temperature of 60 °C, and keep the reaction at this temperature for 8 - 12 h. The gas generated during the reaction is condensed by first-stage water cooling + first-stage freezing condensation. After the reaction is completed, cool the reactor to the material temperature of 0 - 5 °C, discharge the material into a closed pressure filter for pressure filtration (pressure), (part of the aqueous phase of the pressure filtration is recycled and part enters the sewage treatment station); the filter cake is sent to the pulping kettle, add 500 g of dichloromethane, stir and pulp for 1 h, then filter. The filter cake of the pulping is about 400 g and sent to the alkalization process, and the filtrate of the pulping is distilled to recover dichloromethane. The filter cake of the pulping is sent to the alkalization kettle, add 500 g of water, dropwise add about 200 g of 30% liquid alkali under stirring to adjust the pH of the material to 8, add 800 g of dichloromethane, stir and extract for 1 h, let it stand for 0.5 h to separate layers. The lower organic phase is added with 300 g of water, stirred and washed, and then let it stand to separate layers; the separated aqueous phase is distilled to recover dichloromethane and desalt, and the condensed water is sent to the sewage treatment station for treatment. The separated organic phase is discharged into the distillation kettle through a pipeline, and dichloromethane is recovered by atmospheric distillation and recycled. When no distillate is distilled out under atmospheric pressure, carry out vacuum distillation (vacuum degree 0.098 MPa, 60 °C, dry the solvent), and 2-(4-chlorophenoxy)propylhydroxylamine (330.5 g, 78%) is obtained at the bottom of the kettle. Example 2

[0052] S1. Synthesis of methyl 2-(4-chlorophenoxy)propionate is exactly the same as that in Example 1;

[0053] S2. Synthesis of 2-(4-chlorophenoxy)propanol is exactly the same as that in Example 1;

[0054] S3. Synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate;

[0055] Add 500 g of p-toluenesulfonyl chloride and 1,500 g of dichloromethane to the sulfonation reactor, stir for 1 h and set aside. Add 25 g of the catalyst 4-dimethylaminopyridine into the reactor, add a quantitative amount of 500 g of 2-(4-chlorophenoxy)propanol and 400 g of triethylamine, cool to 5-10 °C with ice brine, slowly add the p-toluenesulfonyl chloride and dichloromethane solution, control the reaction temperature below 30 °C, and complete the feeding in 3-4 h. After that, keep the reaction temperature at 25-30 °C and stir for 10 h. After the reaction is completed, add 800 g of water into the reactor, stir and wash, let it stand for layer separation. Add alkali to the upper aqueous phase until pH = 9, recover triethylamine and the catalyst for reuse, and send the water to the sewage treatment station for treatment; discharge the lower organic phase into the distillation kettle, distill at atmospheric pressure, recover dichloromethane by first-stage water cooling + first-stage freezing condensation (-10 °C) for reuse in the reaction, and obtain the product 2-(4-chlorophenoxy)propyl p-toluenesulfonate (786.3 g, yield 86.1%) after distillation. Take 750 g of 2-(4-chlorophenoxy)propyl p-toluenesulfonate, add 1,000 g of DMF, stir evenly, and send it to the next reaction.

[0056] S4、 The synthesis is exactly the same as that in Example 1;

[0057] S5. The synthesis of 2-(4-chlorophenoxy)propylhydroxylamine is exactly the same as that in Example 1. Example 3

[0058] S1. The synthesis of methyl 2-(4-chlorophenoxy)propionate is exactly the same as that in Example 1;

[0059] S2. The synthesis of 2-(4-chlorophenoxy)propanol is exactly the same as that in Example 1;

[0060] S3. The synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate;

[0061] Add 500 g of p-toluenesulfonyl chloride and 1500 g of dichloromethane to the sulfonation reactor, stir for 1 h and set aside. Add 25 g of the catalyst 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine to the reactor, add a quantitative amount of 500 g of 2-(4-chlorophenoxy)propanol and 400 g of triethylamine, cool to 5-10 °C with ice brine, slowly add the p-toluenesulfonyl chloride and dichloromethane solution, control the reaction temperature below 30 °C, and complete the feeding in 3-4 h. After the feeding is completed, maintain the reaction temperature at 25-30 °C and stir for 2 h. After the reaction is completed, add 800 g of water to the reactor, stir and wash, let it stand for layering. Add alkali to the upper aqueous phase until pH = 9, recycle triethylamine and the catalyst for reuse, and send the water to the sewage treatment station for treatment; discharge the lower organic phase to the distillation kettle, distill at atmospheric pressure, recover dichloromethane by first-stage water cooling + first-stage freezing condensation (-10 °C) for reuse in the reaction, and obtain the product 2-(4-chlorophenoxy)propyl p-toluenesulfonate (886.4 g, yield 97.2%) after distillation. Take 750 g of 2-(4-chlorophenoxy)propyl p-toluenesulfonate, add 1000 g of DMF, stir evenly, and send it to the next reaction.

[0062] S4, The synthesis is exactly the same as that in Example 1;

[0063] S5. The synthesis of 2-(4-chlorophenoxy)propylhydroxylamine is exactly the same as that in Example 1. Example 4

[0064] S1. The synthesis of methyl 2-(4-chlorophenoxy)propionate is exactly the same as that in Example 1;

[0065] S2. The synthesis of 2-(4-chlorophenoxy)propanol is exactly the same as that in Example 1;

[0066] S3. The synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate;

[0067] Add 500 g of p-toluenesulfonyl chloride and 1500 g of dichloromethane into the sulfonation reaction kettle, stir for 1 h and set aside. Add 5 g of catalyst 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine into the reaction kettle, add a fixed amount of 500 g of 2-(4-chlorophenoxy)propanol and 400 g of triethylamine, cool down to 5 - 10 °C with ice-salt water, slowly add the p-toluenesulfonyl chloride and dichloromethane solution, control the reaction temperature below 30 °C. After the feeding is completed in 3 - 4 h, keep the reaction temperature at 25 - 30 °C and stir for 4 h. After the reaction is completed, add 800 g of water into the reaction kettle, stir and wash, let it stand for layering. Add alkali to the upper aqueous phase until pH = 9, recycle triethylamine and the catalyst for reuse, and send the water to the sewage treatment station for treatment; discharge the lower organic phase into the distillation kettle, distill at atmospheric pressure, recover dichloromethane by first-stage water cooling + first-stage freezing condensation (-10 °C) for reuse in the reaction. After the distillation is completed, obtain the product 2-(4-chlorophenoxy)propyl p-toluenesulfonate (853.8.4 g, yield 93.5%). Take 750 g of 2-(4-chlorophenoxy)propyl p-toluenesulfonate, add 1000 g of DMF, stir evenly, and send it to the next reaction.

[0068] S4, The synthesis is exactly the same as that in Example 1;

[0069] The synthesis of 2-(4-chlorophenoxy)propylhydroxylamine is exactly the same as that in Example 1.

[0070] The above are only the preferred embodiments of the present invention and are not used to limit the present invention. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art can still modify the technical solutions described in the foregoing embodiments, or perform equivalent replacements for some of the technical features. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included within the protection scope of the present invention.

Claims

1. A production process of 2-(4-chlorophenoxy)propylhydroxylamine, characterized in that, It includes the following steps: S1. Synthesis of methyl 2-(4-chlorophenoxy)propionate Add DMF, 4-chlorophenol, and potassium carbonate to the substitution reaction kettle, heat to 50 - 70 °C, and keep the reaction at this temperature for 1 - 2 h. After the heat preservation ends, add methyl 2-chloropropionate and potassium iodide to the substitution reaction kettle, heat to 60 - 80 °C, and keep the reaction at this temperature for 1 - 3 h. After the reaction ends, perform post-treatment to obtain methyl 2-(4-chlorophenoxy)propionate; S2. Synthesis of 2-(4-chlorophenoxy)propanol Add methanol and methyl 2-(4-chlorophenoxy)propionate to the reduction reaction kettle, keep the temperature in the reaction kettle at 25 - 30 °C, displace with nitrogen, add sodium borohydride, control the reaction temperature at 45 - 50 °C, and keep the reaction at this temperature. After the reaction ends, perform post-treatment to obtain 2-(4-chlorophenoxy)propanol; S3. Synthesis of 2-(4-chlorophenoxy)propyl p-toluenesulfonate Prepare a mixed solution of p-toluenesulfonyl chloride / dichloromethane for use. Add a catalyst, 2-(4-chlorophenoxy)propanol, and triethylamine to the sulfonic acid esterification reaction kettle, cool down to 5 - 10 °C, and slowly add the p-toluenesulfonyl chloride / dichloromethane solution. Control the reaction temperature below 30 °C. After the feeding is completed, keep the reaction temperature at 25 - 30 °C and stir the reaction. After the reaction ends, perform post-treatment to obtain 2-(4-chlorophenoxy)propyl p-toluenesulfonate; The catalyst is 4-dimethylaminopyridine or 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine; S4. Add DMF, hydroxylamine hydrochloride, sodium hydroxide, methyl acetate, and 2-(4-chlorophenoxy)propyl p-toluenesulfonate to the oxime etherification reaction kettle, stir at 20 - 30 °C for 1 - 3 h, heat, and keep the reaction at a certain temperature. After the reaction ends, perform post-treatment to obtain ； S5. Synthesis of 2-(4-chlorophenoxy)propylhydroxylamine Add to the acidification reactor , add water and hydrochloric acid, heat, keep the temperature for reaction, and obtain 2-(4-chlorophenoxy)propylhydroxylamine after post-treatment.

2. The production process of 2-(4-chlorophenoxy)propylhydroxylamine according to claim 1, characterized in that , The mass ratio of the 4-dimethylaminopyridine to 2-(4-chlorophenoxy)propanol is (0.05 - 0.1):

1.

3. The production process of 2-(4-chlorophenoxy)propylhydroxylamine according to claim 1, characterized in that, The mass ratio of the 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine to 2-(4-chlorophenoxy)propanol is (0.01 - 0.1):

1.

4. The production process of 2-(4-chlorophenoxy)propylhydroxylamine according to claim 1, characterized in that, The mass ratio of the 4,4,10,10-tetramethyl-5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-IJ][1,6]naphthyridine to 2-(4-chlorophenoxy)propanol is 0.05:

1.

5. The production process of 2-(4-chlorophenoxy)propylhydroxylamine according to claim 1, characterized in that, The time for the heat preservation reaction in step S2 is 2 - 4 h.

6. The production process of 2-(4-chlorophenoxy)propylhydroxylamine according to claim 1, characterized in that, The time for the stirring reaction in step S3 is 2 - 4 h.

7. The production process of 2-(4-chlorophenoxy)propylhydroxylamine according to claim 1, characterized in that, In step S4, the heating temperature is 60 - 80 °C, and the time for the heat preservation reaction is 8 - 10 h.

8. The production process of 2-(4-chlorophenoxy)propylhydroxylamine according to claim 1, characterized in that, In step S5, the heating temperature is 50 - 70 °C, and the time for the heat preservation reaction is 8 - 12 h.

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