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

HRID 1896633Notes

Reaction equation

HRID 1896633 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.O.[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

6

Reactant 2

HCID 313Hydrochloric AcidHCID 534037522-(Difluoromethoxy)-5-nitropyridine

Product 1

HCID 450909846-(Difluoromethoxy)pyridin-3-amineYield 103.9%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Difluoromethoxy-5-nitro-pyridine obtained in Step A (1.6 g) was treated with iron (5 g) and concentrated hydrochloric acid (0.23 ml) in ethanol (15 ml) and water (2.5 ml) at 80° C. for 20 minutes. Filtration over Celite® and evaporation of the solvent afforded 6-difluoromethoxy-pyridin-3-yl-amine (1.4 g) as an orange solid. 1H NMR (400 MHz, CDCl3) 3.51 (br s, 2H), 6.89 (d, 1H), 7.23 (d, 1H), 7.44 (dd, 1H), 7.80 (d, 1H).

Workup

  1. filtrationFiltration
  2. customover Celite® and evaporation of the solvent

Sources & evidence

ORD record
ord-650829879710481d8e4b02eb2613fb05
Source dataset
uspto-grants-2013_08
Patent number
US08518971B2

Reaction notes

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