3-(4-Cyano-3-nitrobenzoyl)propionic acid → 3-(3-Amino-4-cyanobenzoyl)propionic acid

HRID 596700Notes

Reaction equation

HRID 596700 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])=[CH:5][C:4]=1[N+:16]([O-])=O)#[N:2]>[OH-].[NH4+]>[NH2:16][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:3]=1[C:1]#[N:2])[C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8]

Participants

3

Reactant 1

HCID 214502243-(4-Cyano-3-nitrobenzoyl)propionic acid

Product 1

HCID 214502303-(3-Amino-4-cyanobenzoyl)propionic acid

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent2×

Procedure

A solution of 3-(4-cyano-3-nitrobenzoyl)propionic acid in 5N ammonium hydroxide solution was added to a well stirred boiling aqueous solution of ferrous sulphate. The pH was adjusted to 9 with concentrated ammonium hydroxide solution and the mixture was refluxed for 15 minutes. The filtrate was concentrated and neutralised with glacial acetic acid to give 3-(3-amino-4-cyanobenzoyl)propionic acid.

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5da1985cb0dd4e88ae01916f84a8de32
Source dataset
uspto-grants-1977_03
Patent number
US04011321

Reaction notes

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