3-Nitrophenylacetic acid → (3-Aminophenyl)acetic acid

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Reaction Steps

The 3-nitrophenylacetic acid described in Example 7 is hydrogenated in methanol in the presence of palladium-charcoal to give a yield of 99% of theory of 3-aminophenylacetic acid (m.p. 116°-121° C.). In a manner analogous to that described for the p-compound (see Example 6), there is obtained therefrom, by diazotisation, 3-cyanophenylacetic acid (yield 45% of theory; m.p. 93°-98° C. (decomp.)) and by hydrogenation in dilute hydrochloric acid in the presence of platinum catalyst there is obtained 3-aminomethylcyclohexylacetic acid; yield 66% of theory; m.p. 127°-130° C. The diphosphonic acid is obtained therefrom by means of phosphorus trichloride/phosphorous acid in the manner described in Example 1 in the form of the monohydrate; yield 28% of theory; m.p. 216°-221° C. (decomp.); Mrel =0.27.

Provenance & Evidence