2-Nitro-N-(2-pyridyl)-4-trifluoromethylaniline → 1,2-Benzenediamine, N1-2-pyridinyl-4-(trifluoromethyl)-

HRID 50917

Reaction equation

HRID 50917 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:5]=1[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:16]=[C:15]([C:17]([F:20])([F:18])[F:19])[CH:14]=[CH:13][C:5]=1[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 1

HCID 227366382-Nitro-N-(2-pyridyl)-4-trifluoromethylaniline

Product 1

HCID 227367071,2-Benzenediamine, N1-2-pyridinyl-4-(trifluoromethyl)-Yield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-nitro-N-(2-pyridyl)-4-trifluoromethylaniline (1.00 g, 3.5 mmol), 5% palladium on carbon (0.23 g) and methanol (50 ml) was stirred under a hydrogen atmosphere for 100 min. The mixture was filtered through a pad of celite and the filtrate was concentrated to dryness to give 0.75 g (85%) of the titled compound as yellow brown solids. 1H-NMR (CDCl3) δ: 8.19 (1H, ddd, J=5.1, 1.8, 0.7 Hz), 7.49 (1H, ddd, J=8.3, 7.0, 1.8 Hz), 7.35 (1H, d, J=7.7 Hz), 7.05-7.01 (2H, m), 6.76 (1H, ddd, J=7.0, 5.1, 1.1 Hz), 6.55 (1H, ddd, J=8.3, 1.1, 0.7 Hz), 6.31 (1H, br.s), 3.98 (2H, br.s).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-bf7630fa632a4baaabda797c6593be03
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Linked notes

Loading…