C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/516.6
C07C 53/134 (2006.01) C07C 51/08 (2006.01) C07C 205/56 (2006.01) C07D 263/57 (2006.01)
Patent
CA 1176656
ABSTRACT Hydroxyphenylacetic acids are formed from the corresponding benzaldehydes or alkyl phenyl ketones by reductive amination, cyanation and hydrolysis without isolation or purification of intermediate products. Thus there is provided a process for preparing an acid of the formula Image (I) wherein R is hydrcgen or Cl-C3 alkyl; one of Rl and R2 is hydrogen and the other is hydroxy; provided that R is hydrogen or methyl, when R2 is hydroxy; comprising catalytically hydrogenating a compound of the formula Image in the presence of an amine of the formula HNR3R4 wherein R3 is Cl-C3 alkyl and R4 is hydrogen or Cl-C3 alkyl, in an inert organic solvent to prepare a compound of the formula Image ; adding an alkali metal cyznide to the mixture; holding the mixture at from about 100° to about 150° until a compound of the formula Image is formed; removing the solvent; adding aqueous alkali metal hydroxide; holding the mix- ture at from about 75° to about 125° until the product is formed; and making the mixture acid. These hydroxyphenylacetic acids are useful intermediates in the preparation of pharmacologically active derivatives.
399251
Eli Lilly And Company
Gowling Lafleur Henderson Llp
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