50840-02-3

Usage

InChI:InChI=1/C9H10ClNO2/c1-3-13-9(12)7-6(2)4-5-11-8(7)10/h4-5H,3H2,1-2H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 759-58-0 ethyl isopropylidenecyanoacetate 
• 124571-74-0 1-Carbethoxy-1-cyan-4-dimethylamino-2-methylbuta-1,3-dien 
• 152362-00-0 ethyl 2-chloro-2-cyano-3-methyl-5-oxopentanoate 
• 65996-11-4 1-carbethoxy-1-cyano-2-methyl-4-dimethylamino-1,4-butadiene 

Downstream Products

• 142266-63-5 2-chloro-4-methyl-3-pyridinecarboxylic acid 
• 152362-01-1 2-chloro-4-methyl-3-pyridinecarboxamide 
• 133627-45-9 3-Amino-2-chloro-4-methylpyridine 
• 50839-95-7 2-chloro-4-methylnicotinoylchloride 

Relevant academic research and scientific papers

2-PHENYLNICOTINIC ACID DERIVATIVE

The present invention is to provide the compounds useful as a treating or preventing agent for gout and hyperuricemia which are 2-phenylnicotinic acid derivatives having a uric acid lowering action due to an excellent xanthine oxidase inhibitory action. Since the 2-phenylnicotinic acid derivatives of the present invention exhibit a uric acid lowering action due to an excellent xanthine oxidase inhibitory action and also hypolipemic action, their utility is very high as a treating or preventive agent for gout and hyperuricemia which are often accompanied by hyperlipemia as a complication.

SYNTHESIS OF 3-AMINO-2-CHLORO-4-METHYLPYRIDINE FROM ACETONE AND ETHYL CYANOACETATE

A method for making 3-amino-2-chloro-4-methylpyridine from acetone and ethyl cyanoacetate, as depicted in the following reaction scheme.

Synthesis of 3-amino-2-chloro-4-methylpyridine from acetone and ethyl cyanoacetate

A method for making 3-amino-2-chloro-4-methylpyridine from acetone and ethyl cyanoacetate, as depicted in the following reaction scheme.

Processes for producing 2-Halo-nicotinic acid derivatives and precursors thereto

Disclosed are preferred processes for the preparation of 2-halo-nicotinic acid derivatives of formula (IV): STR1 by cyclocondensation of a 4-halo-4-cyanocarbonyl compound of formula (III): STR2 wherein X is Cl or Br; Y is a carbonyl group and R1, R2 and R3 are each, independently, H, Cl, Br or an organic radical. Further preferred aspects include the preparation of the above-noted 4-halo-4-cyanocarbonyl compound via Michael addition of a 2-halonitrile with an α,β-unsaturated aldehyde or ketone, and the preparation of the 2-halonitrile by redistribution of halogen between a 2,2-dihalonitrile and a parent nitrile.

Regioselective synthesis of 2-chloro 3-pyridinecarboxylates

2-Chlorocyanoacetate was found to undergo base-catalyzed Michael addition to α,β-unsaturated ketones or aldehydes to afford 5-oxopentenenitrile derivatives. In the presence of anhydrous HCl, these compounds cyclize to yield 2-chloro-3-pyridinecarboxylates. The process is highly regiospecific and useful in the synthesis of 2,3-disubstituted pyridines.

Preparation of 2-chloropyridine 3-carboxylic acid esters

2-chloropyridine 3-carboxylic acid esters are prepared by cyclization of 1,3-butadiene derivatives in the presence of hydrogen chloride.