2-Chloro-5-nitro-3-(trifluoromethyl)pyridine → 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

HRID 41976Notes

Reaction equation

HRID 41976 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([N+:12]([O-])=O)=[CH:4][N:3]=1>C(OCC)(=O)C.[Zn+2].[Br-].[Br-]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH2:12])=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

4

Reactant 1

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Product 1

HCID 135322446-Chloro-5-(trifluoromethyl)pyridin-3-amineYield 92.1%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (5.25 mmol, 1.19 g), ZnBr2 (1.05 mmol, 0.200 g) and 5% Pt (C) (1.58 mmol, 0.31 g) in ethyl acetate (50 ml) was stirred for 20 hours under hydrogen atmosphere. The catalyst was filtered off and the solid was washed with warmed ethanol. The solvent was evaporated affording the expected product (0.95 g, yield 92%).

Workup

  1. filtrationThe catalyst was filtered off
  2. washthe solid was washed with warmed ethanol
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-dd5d5aedb746487fad31455fd2cacb7e
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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