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

HRID 1898311Notes

Reaction equation

HRID 1898311 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.Cl>C(O)C.[Fe]>[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 313Hydrochloric AcidHCID 534037522-(Difluoromethoxy)-5-nitropyridine

Product 1

HCID 450909846-(Difluoromethoxy)pyridin-3-amineYield 106.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(difluoromethoxy)-5-nitropyridine (0.900 g, 2.35 mmol) in ethanol (5.0 mL), was added iron powder (0.400 g, 7.14 mmol) and conc. HCl (0.2 mL). The reaction mass was refluxed for ½ h. Ethanol was removed under vacuum. To the reaction mass, water was added, basified with NaHCO3 and extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.400 g of the desired product. 1HNMR (DMSO-d6): δ 7.65 (s, 1H), 7.52-7.03 (t, J=72.0 Hz, 1H), 7.27 (s, 1H), 6.73 (d, J=8.4 Hz, 1H); MS [M−H]−: 159.14.

Workup

  1. temperatureThe reaction mass was refluxed for ½ h
  2. customEthanol was removed under vacuum
  3. additionTo the reaction mass, water was added
  4. extractionextracted with DCM
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3dbd407e261a4c4da58fb600a23f0526
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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