2-Fluoro-3-methyl-5-nitropyridine → 6-Fluoro-5-methylpyridin-3-amine

HRID 3316Notes

Reaction equation

HRID 3316 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][N:3]=1>CCO.[Pd]>[NH2:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([F:1])=[N:3][CH:4]=1

Participants

4

Reactant 1

HCID 124081842-Fluoro-3-methyl-5-nitropyridine

Product 1

HCID 219526916-Fluoro-5-methylpyridin-3-amineYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Fluoro-3-methyl-5-nitropyridine (8.2 g, mmol) was combined with 5% Pd/C (100 mg) in EtOH (100 mL) under a H2 atmosphere for 16 hours. The mixture was filtered and concentrated, and the crude product was chromatographed (silica gel; CHCl3 /MeOH 99:1 to 96:4) to afford a solid (5.2 g, 78% ): 1H NMR (DMSO-d6, 300 MHz) δ2.10 (s, 3H), 5.11 (brs, 2H), 6.95 (dd, J=8.14 Hz, 1H), 7.26 (t, J=2.72 Hz, 1H); MS (CI/NH3) m/z: 127 (M+H)+, 144 (M+NH4)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe crude product was chromatographed (silica gel; CHCl3 /MeOH 99:1 to 96:4)

Sources & evidence

ORD record
ord-8caea27682284e0fa725f4c5568af18a
Source dataset
uspto-grants-1998_03
Patent number
US05733912

Reaction notes

Loading…