HCID 13799940, compound → 2-(3-Cyanophenyl)acetic acid

HRID 2413696Notes

Reaction equation

HRID 2413696 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][C:10]([OH:12])=[O:11])[CH2:4]1>Cl.[Pt]>[C:2]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:1]

Participants

4

Reactant 1

HCID 13799940HCID 13799940, compound

Product 1

HCID 15193972-(3-Cyanophenyl)acetic acidYield 45%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 313Hydrochloric AcidSolvent

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.

Workup

  1. customthere is obtained

Sources & evidence

ORD record
ord-32c302806c634a85b14852b4dfbe3034
Source dataset
uspto-grants-1988_01
Patent number
US04719203

Reaction notes

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