Ammonia → 5-(Trifluoromethyl)pyridin-3-amine
Reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[NH3:12]>O.[Cu]Cl>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:7]=[C:2]([NH2:12])[CH:3]=[N:4][CH:5]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 170 °C
Procedure
Prepared according to the method of Barlin et al., Aust. J Chem., 1990, 43, 1175: 3-Chloro-5-(trifluoromethyl)pyridine (3.0 g, 16.52 mmol) is suspended in water (67.5 ml) and treated with copper(I)chloride (8.18 g, 82.62 mmol). Aqueous ammonia solution (25%, 67.5 ml) is added, and the reaction is stirred for 48 hours at 170° C. in the autoclave. The reaction mixture is cooled to room temperature and extracted three times with dichloromethane. The combined organic phases are washed with brine, dried with magnesium sulphate, filtered and concentrated in vacuo to yield analytically pure product.
Workup
- customPrepared
- temperatureThe reaction mixture is cooled to room temperature
- extractionextracted three times with dichloromethane
- washThe combined organic phases are washed with brine
- dry with materialdried with magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto yield analytically pure product
Sources & evidence
- ORD record
- ord-760322e298d24993ab5c2a17ce3e0295
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07230017B2
Reaction notes
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