Synthetic method for indole-3-carboxaldehyde compounds

A technology of indole formaldehyde and synthesis method, applied in the direction of organic chemistry, etc.

Active Publication Date: 2012-11-21
FUJIAN TIANFU BIOTECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] literature (Synlett, 2008 (13), 2023-2027) reported that 3-indole carbinol was oxidized by PCC as raw material to obtain 3-indole formaldehyde. Post-processing is difficult, not suitable for industrial production

Method used

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  • Synthetic method for indole-3-carboxaldehyde compounds
  • Synthetic method for indole-3-carboxaldehyde compounds
  • Synthetic method for indole-3-carboxaldehyde compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add o-methylaniline (10 g, 93 mmol) and 10 ml of DMF into the flask, and slowly add 20 ml of Vilsmeier reagent prepared dropwise at 0°C. After the dropwise addition, stir at room temperature (about 25°C) for 1 hour. Then the temperature was raised to 85° C., and the reaction was heated for 5 hours. After the completion of the detection reaction, a saturated sodium carbonate solution was added until it was alkaline, and a large amount of solids were precipitated, filtered, and dried to obtain 12.4 grams of solids, with a yield of 96%. The resulting product had a melting point of 198-199°C.

[0035] 1 H NMR (DMSO-d 6 ) 12.14 (1H, broad), 9.95 (1H, s), 8.30-8.09 (2H, m), 7.56-7.20 (3H, m); 13 C NMR (DMSO-d 6 ) 185.34, 138.85, 137.43, 124.49, 123.84, 122.50, 121.20, 118.54, 112.80.

[0036] Example 2

Embodiment 2

[0038] 4-Amino-3-methylphenol (15 g, 121.8 mmol) and 10 ml of DMF were added to the flask, and 20 ml of the prepared Vilsmeier reagent was slowly added dropwise at 0°C. After the dropwise addition was complete, stir at room temperature for 1 hour. Then the temperature was raised to 85° C., and the reaction was heated for 7 hours. After completion of the reaction, saturated sodium carbonate solution was added until it was alkaline, and a large amount of solids were precipitated. After filtration and drying, 18 grams of solids were obtained, with a yield of 92%. The resulting product had a melting point of 235°C.

[0039] 1 H NMR (DMSO-d 6 ) δ: 11.89 (1H, s), 9.84 (1H, s), 9.07 (1H, s), 8.13 (1H, s), 7.48 (1H, d), 7.29 (1H, d), 6.73 (1H, dd ).

[0040] Example 3

Embodiment 3

[0042] 2,3-Dimethyl-aniline (10 g, 82.5 mmol) and 10 ml of DMF were added to the flask, and 25 ml of the prepared Vilsmeier reagent was slowly added dropwise at 0°C. After the dropwise addition was complete, stir at room temperature for 1 hour. Then the temperature was raised to 85° C., and the reaction was heated for 7 hours. After the reaction was complete, saturated sodium carbonate solution was added until it was alkaline, and a large amount of light yellow solids were precipitated, which were filtered and dried to obtain 11.8 g of solids, with a yield of 90%. The resulting product had a melting point of 198-199°C.

[0043] 1 H NMR (DMSO-d6, 400 MHz) δ: 12.51(1H, broad), 9.97 (1H, s), 7.34 (1H, d), 7.20 (1H, d), 6.98 (1H, d), 6.73 (1H , d), 2.35 (3H, s).

[0044] Example 4

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PUM

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Abstract

The invention discloses a synthetic method for indole-3-carboxaldehyde compounds. The synthetic method comprises the following steps: (1) using anhydrous dimethylformamide as a solvent, and slowly adding phosphorus oxychloride, and agitating for 30 minutes at 0 to 5 DEG C so as to obtain a Vilsmeier agent; (2) using the anhydrous dimethylformamide as the solvent, adding 2-methylaniline compounds shown in the formula (I), dropping the Vilsmeier agent prepared in step (1) at 0 to 5 DEG C, agitating for 1 to 2 hours at room temperature after dropping, and heating for reflux to react for 5 to 8 hours; and (3) cooling after the reaction, adding a saturated sodium carbonate solution to adjust to alkalinity, filtering the precipitated solid, an drying to obtain a product, and finally recrystallizing the product to obtain the indole-3-carboxaldehyde compounds as shown in the formula (II). The method disclosed by the invention is simple to operate, and low in cost of production, and is not only suitable for small-scale preparation in a laboratory, but also suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a synthesis method of a class of 3-indole formaldehyde heterocyclic compounds, in particular to a synthesis method of 3-indole formaldehyde compounds. Background technique [0002] In the prior art, some of the disclosed 3-indole formaldehyde heterocyclic compounds are important intermediates for the synthesis of many drugs, such as sumatriptan, naratriptan, zolmitriptan, ritriptan, etc. for the treatment of neurological diseases. Zatriptan; the lipid-lowering drug fluvastatin; ondansetron for the treatment of carcinoid syndrome, etc. 3-Indolecarboxaldehyde is one of the best-selling benzo five-membered heterocyclic compounds on the market. [0003] 3-Indolecarboxaldehyde has been reported in the literature and has a variety of synthetic methods, the most important of which is to synthesize indole as a raw material. First, some substituted anilines are used as raw materials to synthesize indole by high-temperature and high-pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12
Inventor 刘现军张中剑
Owner FUJIAN TIANFU BIOTECH DEV CO LTD
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