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

HRID 367070Notes

Reaction equation

HRID 367070 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:4]=[N:3][C:2]([F:1])=[C:7]([CH3:8])[CH:6]=1

Participants

4

Reactant 1

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

Product 1

HCID 219526916-Fluoro-5-methylpyridin-3-amineYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Fluoro-3-methyl-5-nitropyridine (from Step 32b above) was combined with 100 mg of 5% Pd/C in EtOH (100 mL), and the mixture was stirred under an atmosphere of hydrogen for 16 hours. The mixture was filtered and concentrated. The crude product was chromatographed (silica gel; CHCl3 /MeOH, 99:1 to 94:6) to yield 5.2 g (78%) of the title compound: 1H NMR (DMSO-d6, 300 MHz) δ 7.26 (t, J=2.7 Hz, 1H), 6.95 (dd, J=8.1 Hz, 1H), 5.11 (br, s, 2H), 2.10 (s, 3H); 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 94:6)

Sources & evidence

ORD record
ord-a53cb044ae61438d9607d8c6a4546962
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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