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

HRID 2413695Notes

Reaction equation

HRID 2413695 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 158763-Nitrophenylacetic acid

Product 1

HCID 571807(3-Aminophenyl)acetic acidYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-df530719803e4c93b699142560e41d89
Source dataset
uspto-grants-1988_01
Patent number
US04719203

Reaction notes

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