Hydrochloric Acid → 6-(Difluoromethoxy)pyridin-3-amine
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]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
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
- filtrationFiltration
- 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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