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

HRID 217278Notes

Reaction equation

HRID 217278 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-07561f2678fc4369b4745da9f722f65b
Source dataset
uspto-grants-2012_06
Patent number
US08193362B2

Reaction notes

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