(5-Fluoro-2-nitrophenyl)pyridin-3-ylamine → 4-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

HRID 242962Notes

Reaction equation

HRID 242962 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:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=1>CCO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58459332(5-Fluoro-2-nitrophenyl)pyridin-3-ylamine

Product 1

HCID 584592164-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a mixture of (5-fluoro-2-nitrophenyl)pyridin-3-yl-amine (25 mmol) in EtOH (300 mL) was added 10% Pd/C (1.0 g) and the reaction mixture stirred at RT under a hydrogen atmosphere for 18 h. Additional Pd/C (1.0 g) was added and stirring at RT under a hydrogen atmosphere continued for 2 h. The suspension was filtered through a pad of Celite® and the filtrate was concentrated in vacuo to afford the title compound as a brown solid (quantitative). 1H NMR (CDCl3, 300 MHz): δ 8.27 (1H, dd, J=2.64, 0.91 Hz), 8.15 (1H, dd, J=4.41, 1.71 Hz), 7.20-7.09 (2H, m), 6.87 (1H, dd, J=9.61, 2.59 Hz), 6.80-6.68 (2H, m), 5.50 (1H, br s), 2.96 (2H, br s)

Workup

  1. stirringstirring at RT under a hydrogen atmosphere
  2. waitcontinued for 2 h
  3. filtrationThe suspension was filtered through a pad of Celite®
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-19fbde9558864de8b63fa234d5d6a953
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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