(3-Fluoro-2-methyl-6-nitro-phenyl)-pyridin-2-ylamine → 4-Fluoro-3-methyl-N2-pyridin-2-yl-benzene-1,2-diamine

HRID 243060Notes

Reaction equation

HRID 243060 reaction equation
[F:1][C:2]1[C:3]([CH3:18])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:5]([N+:8]([O-])=O)=[CH:6][CH:7]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:3]([CH3:18])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:5]([NH2:8])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68157526(3-Fluoro-2-methyl-6-nitro-phenyl)-pyridin-2-ylamine

Product 1

HCID 681580774-Fluoro-3-methyl-N2-pyridin-2-yl-benzene-1,2-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-fluoro-2-methyl-6-nitro-phenyl)-pyridin-2-yl-amine (2 g, 8.1 mmol) in EtOAc (25 mL) was added palladium on carbon (200 mg, 10% by wt) and the reaction mixture stirred at RT under an atmosphere of hydrogen for 16 h. The reaction mixture was filtered and the filtrate concentrated in vacuo to give the title compound as a white solid (1.7 g, 100%). 1H NMR 400 MHz δ (CDCl3): 8.19-8.11 (1H, m), 7.42 (1H, ddd, J=8.8, 7.1, 2.0 Hz), 6.86 (1H, t, J=8.9 Hz), 6.69 (1H, dd, J=6.9, 5.1 Hz), 6.61 (1H, dd, J=8.8, 5.4 Hz), 6.16 (1H, d, J=8.3 Hz), 6.07 (1H, br s), 3.76 (2H, br s), 2.10 (3H, d, J=1.9 Hz).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-edea18b42e2c418fa3bcd72e5e070297
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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