Ammonia → 2-Amino-3-(trifluoromethyl)pyridine

HRID 2238638Notes

Reaction equation

HRID 2238638 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH3:12]>>[F:9][C:8]([F:11])([F:10])[C:7]1[C:2]([NH2:12])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Conditions

Temperature
175 °C

Procedure

10 g of 2-chloro-3-trifluoromethylpyridine was dissolved in 100 mL of 25% aqueous ammonia, and stirred in a sealed-tube at 175° C. for 3 days. The reaction mixture was cooled back to room temperature, and was extracted with diethyl ether. The organic layer was washed with water and with saturated brine in the subsequent order, and then dried over anhydrous sodium sulfate. After filtering the insolubles, the filtrate was concentrated under reduced pressure to obtain 8.73 g of 3-(trifluoromethyl)-2-pyridinamine [34-1] as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled back to room temperature
  2. extractionwas extracted with diethyl ether
  3. washThe organic layer was washed with water and with saturated brine in the subsequent order
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtering the insolubles
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-84a42efce6b94ff4ab9c4cdfc83e7c9f
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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