Process for preparing anthranylaldehyde derivatives

Details Process for preparing anthranylaldehyde derivatives Process for preparing anthranylaldehyde derivatives

C - Chemistry, Metallurgy

07

D

260/566.6

C07D 263/04 (2006.01) C07D 233/02 (2006.01)

Patent

CA 1113120

ABSTRACT OF THE DISCLOSURE: The present invention is concerned with a process for preparing an anthranylaldehyde derivative of formula: Image (wherein Z1 and Z2 are same or different each other and each represent a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group; Z1 is attached to ortho position to the amino group and Z2 may be positioned at any of 3-, 4-, 5- and 6-positions.), which comprises steps of (1) reacting a o-halogenobenzaldehyde of formula: Image (wherein X represents a halogen atom.) with an alkylamine derivative of formula: Image (wherein R and R1 each represents a lower alkyl group; Y represents a nitrogen, oxygen or sulfur atom; m represents an integer of 2 or 3; n represents 0 or 1, provided that n is 1 when Y is a nitrogen atom and n is 0 when Y is an oxygen or sulfur atom.), affording a compound of formula: Image (wherein X, R, R1, m and n are as defined above.), (2) reacting the thus obtained compound with an aniline derivative of formula: Image (wherein Z1 and Z2 are as defined above.), giving a condensation product having the following formula: Image (wherein y, Z1, Z2, R, R1, m and n are defined as above.) and, (3) treating the thus obtained condensation product with an acid. The anthranylaldehyde derivatives, i.a. N-(2,6-dichlorophenyl)anthranylaldehyde is useful as an intermediate for preparation of the corresponding anilinophenylacetic acids which are anti-inflammatory and analgesic agents.

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