(5-Fluoro-2-nitrophenyl)pyridin-2-yl-amine → 4-Fluoro-N2-pyridin-2-ylbenzene-1,2-diamine

HRID 242942Notes

Reaction equation

HRID 242942 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][N: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][N:10]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68157116(5-Fluoro-2-nitrophenyl)pyridin-2-yl-amine

Product 1

HCID 681571794-Fluoro-N2-pyridin-2-ylbenzene-1,2-diamineYield 108.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (5-fluoro-2-nitrophenyl)pyridin-2-yl-amine (255 mg, 1.09 mmol) in EtOAc (20 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (28 mg) and was stirred at RT under a hydrogen atmosphere for 18 h. The suspension was filtered through a phase separator and the filtrate concentrated in vacuo to afford the title compound as a black solid (241 mg, quantitative). 1H NMR (CDCl3, 400 MHz): δ 8.20-8.16 (1H, m), 7.51-7.44 (1H, m), 7.12-7.07 (1H, m), 6.78-6.72 (3H, m), 6.55 (1H, dt, J=8.39, 0.93 Hz), 6.22 (1H, s), 3.63 (2H, s).

Workup

  1. customwas degassed with a stream of nitrogen
  2. additionto addition of 10% Pd/C (28 mg)
  3. filtrationThe suspension was filtered through a phase separator
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-feac5f7601ef465f9dc7b2f48a0796ef
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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