Process for producing 4-trifluoromethylnicotinic acid

Details Process for producing 4-trifluoromethylnicotinic acid Process for producing 4-trifluoromethylnicotinic acid

C - Chemistry, Metallurgy

07

D

C07D 213/80 (2006.01) C07C 45/45 (2006.01) C07C 45/70 (2006.01) C07C 49/255 (2006.01) C07C 221/00 (2006.01) C07C 225/14 (2006.01) C07C 229/22 (2006.01) C07C 229/30 (2006.01) C07C 251/08 (2006.01)

Patent

CA 2176788

A process for producing 4-trifluoromethylnicotinic acid of the formula (VIII) or its salt: (see formula I) which comprises (i) a first step of reacting a halide of the formula (I): CF3COHal (I) wherein Hal is a halogen atom, with a compound of the formula (II): CH2=CHOR1 (II) wherein R1 is an alkyl group, in the presence of a base to obtain a 4-alkoxy-1,1,1-trifluoro-3-buten-2-one of the formula (III): CF3CO-CH=CH-OR1 (III) wherein R1 is as defined above, and reacting this compound with ammonia to obtain 4-amino-1,1,1-trifluoro- 3-buten-2-one of the formula (IV): Image and (ii) a second step of subjecting the 4-amino-1,1,1- trifluoro-3-buten-2-one obtained in the first step and a compound of the formula (V): ACO2R2 (V) wherein R2 is an ester-forming residue, and A is (R3O)CH=CH- or (R30)2CHCH2-, wherein R3 is an alkyl group, to a condensation reaction to obtain a compound of the formula (VI) (inclusive of its salt): Image wherein R2 is as defined above, and/or a compound of the formula (VII) (inclusive of its salt): Image wherein R2 and R3 are as defined above, as the reaction product, and then subjecting the reaction product to ring closure and hydrolysis.

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