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

HRID 2042677Notes

Reaction equation

HRID 2042677 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-b3065a3539594c55990c0f30d96424fa
Source dataset
uspto-grants-2013_11
Patent number
US08586593B2

Reaction notes

Loading…