Acetic Acid → 6-(Difluoromethoxy)pyridin-3-amine

HRID 250029Notes

Reaction equation

HRID 250029 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][N:5]=1.C(O)(=O)C>CO.[Pd]>[F:13][CH:2]([F:1])[O:3][C:4]1[N:5]=[CH:6][C:7]([NH2:10])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 534037522-(Difluoromethoxy)-5-nitropyridine

Product 1

HCID 450909846-(Difluoromethoxy)pyridin-3-amineYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2-(difluoromethoxy)-5-nitropyridine (4.7 g, 24.7 mmol) in degassed methanol (100 mL) was added 10% palladium on carbon (500 mg, 0.47 mmol) and the reaction was hydrogenated at atmospheric pressure for 1 hour. To this was added acetic acid (2.83 mL, 49.4 mmol) and the reaction was filtered through Celite and concentrated in vacuo to afford 6-(difluoromethoxy)pyridin-3-amine (6.33 g, 25.9 mmol, 105% yield) as an olive green liquid. 1H NMR (400 MHz, MeOD-d4) δ ppm 7.60 (d, J=2.76 Hz, 1 H), 7.37 (s, 0.5 H), 7.15 (dd, J=8.66, 2.89 Hz, 1 H), 7.00 (s, 0.5H), 6.71 (d, J=8.78 Hz, 1 H).

Workup

  1. filtrationthe reaction was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2e6e407a74b4944b16ca8fb7dc37b66
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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