Ammonia → 5-(Trifluoromethyl)pyridin-3-amine

HRID 1766355Notes

Reaction equation

HRID 1766355 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]=1

Participants

5

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

  1. customPrepared
  2. temperatureThe reaction mixture is cooled to room temperature
  3. extractionextracted three times with dichloromethane
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried with magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. 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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