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

HRID 911278

反応式

HRID 911278 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-6c5c2c4d22d44ba9b728fce81a9e5bda
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

関連ノート

読み込み中…