Ammonia → (2,2-dimethyl-2H-chromen-6-yl)methanamine

HRID 911278

반응식

HRID 911278 반응식
[CH3:1][C:2]1([CH3:14])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[N:13])[CH:8]=2)[O:3]1.C(O)C.N>CO.[Ni]>[NH2:13][CH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:14])([CH3:1])[CH:11]=[CH:10]2

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 702EthanolHCID 27790742,2-dimethyl-2H-1-benzopyran-6-carbonitrile

생성물 1

HCID 55255597(2,2-dimethyl-2H-chromen-6-yl)methanamine수율 97.9%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

Add 2,2-dimethyl-2H-chromene-6-carbonitrile (1.5 g, 8.1 mmol) and ethanol wet Raney® activated nickel (0.4 g) to a Parr pressure vessel. Immediately add 7N ammonia in methanol (170 mL) and seal the vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (3400 KPa), seal the vessel, agitate the reaction and heat to 60° C. for 20 h. 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. Purify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (9:1) to obtain the title compound (1.5 g, 97%). MS (ES+) m/z: 175 M+H−NH3)+.

후처리

  1. customPurge the reaction vessel with nitrogen
  2. customseal the vessel
  3. customthe reaction
  4. temperatureheat
  5. temperatureto cool to ambient temperature
  6. customVent the excess hydrogen from the vessel and purge the vessel with nitrogen
  7. filtrationFilter the reaction mixture
  8. customto remove the Raney® nickel
  9. customPurify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (9:1)

출처 및 근거

ORD 기록
ord-6c5c2c4d22d44ba9b728fce81a9e5bda
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

연결된 노트

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