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

HRID 1637262Notes

Reaction equation

HRID 1637262 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-37ef211d2353457ab1a9339bb6a5135d
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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