Ammonia → 1-[4-(Trifluoromethyl)pyridin-3-yl]methanamine

HRID 911311노트

반응식

HRID 911311 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[C:8]([C:9]#[N:10])=[CH:7][N:6]=[CH:5][CH:4]=1.N>[Ni].C(O)C>[NH2:10][CH2:9][C:8]1[CH:7]=[N:6][CH:5]=[CH:4][C:3]=1[C:2]([F:12])([F:1])[F:11]

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 27367434-(Trifluoromethyl)pyridine-3-carbonitrile

생성물 1

HCID 35238171-[4-(Trifluoromethyl)pyridin-3-yl]methanamine수율 55%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

반응 조건

온도
40 °C

실험 절차

Add 4-trifluoromethyl-nicotinonitrile (1.0 g, 5.8 mmol) and ethanol wet Raney® activated nickel (0.2 g) to a Parr pressure vessel. Immediately add, at ambient temperature, 2B-ethanol (25 mL) previously saturated with ammonia gas and seal the vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 KPa), seal the vessel, agitate the reaction and heat to 40° C. Continue the reaction for 20 h then turn off the heat and allow the reaction mixture to cool to ambient temperature. Vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Filter the reaction mixture to remove the Raney® nickel, wash with ethanol and concentrate in vacuo. Purify by SCX chromatography to give the title compound (560 mg, 55%). MS (ES+) m/z: 177 (M+H)+.

후처리

  1. additionImmediately add, at ambient temperature
  2. customPurge the reaction vessel with nitrogen
  3. customseal the vessel
  4. customthe reaction
  5. customthe reaction for 20 h
  6. temperatureheat
  7. temperatureto cool to ambient temperature
  8. customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
  9. filtrationFilter the reaction mixture
  10. customto remove the Raney® nickel
  11. washwash with ethanol
  12. concentrationconcentrate in vacuo
  13. customPurify by SCX chromatography

출처 및 근거

ORD 기록
ord-6320d766e7a44decb171eacc796f99f2
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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