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Process for the preparation of 2-aminomriordan peter dominic ethylpyridines

A technology of haloalkyl and alkoxycarbonyl, which is applied in the field of preparing 2-aminomethylpyridine, and achieves the effect of high yield and easy handling

Inactive Publication Date: 2008-02-13
BAJER KROPSAJENS LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is still a method that requires recycling of the activator and aprotic solvent to minimize the cost of the industrial scale process

Method used

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  • Process for the preparation of 2-aminomriordan peter dominic ethylpyridines
  • Process for the preparation of 2-aminomriordan peter dominic ethylpyridines
  • Process for the preparation of 2-aminomriordan peter dominic ethylpyridines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1 (method A)

[0061] A mixture of 3-chloro-2-cyano-5-trifluoromethylpyridine (5.1 g) and 5% palladium on charcoal (5.1 mg palladium metal) with methanol and conc. Hydrochloric acid (2.5 mL) was mixed with stirring. After 4 hours, the reaction was judged to be complete by high performance liquid chromatography (hplc). The mixture was filtered through celite, washed with water and methanol, and evaporated to form the hydrochloride salt of 2-aminomethyl-3-chloro-5-trifluoromethylpyridine in 95-97% yield, NMR (at D. 2 O), 4.6 (s, 2H), 8.35 (s, 1H), 8.9 (s, 1H).

Embodiment 2

[0062] Embodiment 2 (method B)

[0063] A solution of potassium cyanide (71.6 g) in water (215 g) was added to 3-chloro-2-fluoro-5-trifluoromethylpyridine (199.5 g) and Aliquat 336 (chloro trioctanoylmethylamine, 12.1 g) in a stirred mixture. Stirring was continued at this temperature for 4 hours until the amount of starting fluoride by hplc was below 1%. The lower organic phase was separated off and washed with aqueous sodium chloride and distilled at 15 mbar at 90°C to give 3-chloro-2-cyano-5-trifluoromethylpyridine (185.8 g, 90% yield) . The product was 98% pure.

Embodiment 3

[0064] Embodiment 3 (method B)

[0065] Add solid sodium cyanide (0.29 g) to a stirred mixture of 3-chloro-2-fluoro-5-trifluoromethylpyridine (0.8 g) and tetrabutylammonium bromide (0.06 g) at 20-25°C , and stirred for 23 hours to give 3-chloro-2-cyano-5-trifluoromethylpyridine (0.68 g, 82% yield by hplc).

[0066] Example of Step (D)

[0067] At 110°C, 2,3-dichloro-5-trifluoromethylpyridine (800 g) was added to a stirred mixture of anhydrous potassium fluoride (320 g) and anhydrous dimethyl sulfoxide, and then at 120° C. Heating for 2 hours and fractional distillation under reduced pressure gave 3-chloro-2-fluoro-5-trifluoromethylpyridine (685 g) in 92% yield (98% purity).

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Abstract

The invention relates to a process for the preparation of a compound of formula (V), according to the following scheme: wherein the various substituants are as defined in the description.

Description

technical field [0001] The present invention relates to a new process for the preparation of 2-aminomethylpyridines, especially 2-aminomethyl-3-chloro-5-trifluoromethylpyridine, and the 2-cyanopyridines used in their preparation, The above-mentioned compounds can be used as intermediates for the preparation of insecticides. Background technique [0002] Catalytic reduction of cyanopyridines is known to provide aminomethylpyridines. However, when the cyanopyridine compound contains an additional halogen atom, the reduction reaction is complicated by competing dehalogenation reactions. In P.N.Rylander's "Hydrogenation Methods" (Best Synthetic Series, Academic Press publication), (1985), it is mentioned on page 148 that when it is desired to carry out a dehalogenation reaction, palladium is usually selected as a catalyst, while platinum and rhodium are relatively Does not work, so it is often used in hydrogenation reactions when it is necessary to retain the halogen. [0003...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/61C07D213/26C07D213/84
CPCC07D213/26C07D213/61C07D213/84
Inventor N·丹恩P·D·赖尔登M·R·阿明M·梅勒
Owner BAJER KROPSAJENS LTD