5-Fluoro-2-nitro-N-phenylaniline → 4-Fluoro-2-phenylaminoaniline

HRID 242788Notes

Reaction equation

HRID 242788 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1>CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 189929835-Fluoro-2-nitro-N-phenylaniline

Product 1

HCID 214506204-Fluoro-2-phenylaminoaniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (5-fluoro-2-nitrophenyl)phenylamine (1.37 g, 5.90 mmol) in IMS (50 mL) and EtOAc (50 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (138 mg) and was stirred at RT under a hydrogen atmosphere for 4 h. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo affording 4-Fluoro-N2-phenylbenzene-1,2-diamine as a red oil (1.19 g, quantitative). LCMS: RT 2.87 min [M+H]+ 203.1.

Workup

  1. customwas degassed with a stream of nitrogen
  2. additionto addition of 10% Pd/C (138 mg)
  3. filtrationThe suspension was then filtered through a PTFE frit
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-32e6ffe99116452599541d1304e9a555
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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