4-Nitro-3-phenylaminobenzonitrile → 4-Amino-3-phenylaminobenzonitrile

HRID 242801Notes

Reaction equation

HRID 242801 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-])=O>CCOC(C)=O.O=[Pt]=O>[NH2:1][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 681579814-Nitro-3-phenylaminobenzonitrile

Product 1

HCID 681572074-Amino-3-phenylaminobenzonitrile

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitro-3-phenylaminobenzonitrile (560 mg, 2.34 mmol) in EtOAc (30 mL) was degassed with a stream of nitrogen, prior to addition of PtO2 (44 mg), and was stirred at RT under a hydrogen atmosphere for 2 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo affording 4-Amino-3-phenylaminobenzonitrile as a purple solid (500 mg, quantitative). LCMS: RT 3.20 min [M+H]+ 210.1.

Workup

  1. filtrationThe suspension was then filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4cd45a9abba945c09b938012752b6c09
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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