Water → 5-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637262ノート

反応式

HRID 1637262 の反応式
[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:18](=O)[CH2:17][CH2:16][C:15]=2[C:14]=34)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:26].[Na+].O>C(Cl)Cl.CO>[NH2:26][CH:18]1[C:13]2[C:14]3[C:15](=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[NH:8][C:9]=3[CH:10]=[CH:11][CH:12]=2)[CH2:16][CH2:17]1

参加物

7

反応物 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

生成物 1

HCID 101988185-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole収率 52%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A portion (2.3 g) of the compound obtained in Example 41 was dissolved in a mixed solvent of methylene chloride (450 ml) and methanol (450 ml) and to the solution were added ammonium acetate (7.12 g) and sodium cyanoborohydride (0.76 g). The mixture was stirred for 3 days at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1) to yield 1.2 g (52%) of the titled compound as pale brown crystals.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1)

出典と根拠

ORDレコード
ord-37ef211d2353457ab1a9339bb6a5135d
出典データセット
uspto-grants-2000_03
特許番号
US06040331

反応ノート

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