(2-Fluoro-6-nitrophenyl)phenylamine → 3-Fluoro-N2-phenylbenzene-1,2-diamine

HRID 242784Notes

Reaction equation

HRID 242784 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 69251985(2-Fluoro-6-nitrophenyl)phenylamine

Product 1

HCID 692512983-Fluoro-N2-phenylbenzene-1,2-diamineYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (2-fluoro-6-nitrophenyl)phenylamine (558 mg, 6.57 mmol) and 10% Pd/C (115 mg) in IMS (20 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 2 h. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo affording 3-Fluoro-N2-phenylbenzene-1,2-diamine as a white solid (468 mg, 96%). 1H NMR (CDCl3, 400 MHz): δ 7.24-7.16 (2H, m), 7.04-6.96 (1H, m), 6.83 (1H, t, J=7.37 Hz), 6.66 (2H, d, J=7.95 Hz), 6.59-6.48 (2H, m), 5.16 (1H, bs), 3.96 (2H, s).

Workup

  1. customwas degassed with a stream of nitrogen
  2. filtrationThe suspension was then filtered through a PTFE frit
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-52d9244654af43c897f5ea4dee039018
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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