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

HRID 2041199ノート

反応式

HRID 2041199 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c085d21965ee4c55a32e7d730eb14220
出典データセット
uspto-grants-2013_11
特許番号
US08580780B2

反応ノート

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