1-Benzoyl-1,2,2a,5-tetrahydrobenzo[cd]indol-4(3H)-one → (4-Amino-2a,3,4,5-tetrahydrobenz[cd]indol-1(2H)-yl)phenylmethanone

HRID 2420259Notes

Reaction equation

HRID 2420259 reaction equation
[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH2:18][C:19](=O)[CH2:20][CH:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>C(O)C>[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH2:18][CH:19]([NH2:28])[CH2:20][CH:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2956641-Benzoyl-1,2,2a,5-tetrahydrobenzo[cd]indol-4(3H)-oneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 14347825(4-Amino-2a,3,4,5-tetrahydrobenz[cd]indol-1(2H)-yl)phenylmethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction mixture was prepared from 2.7 g. of 1-benzoyl-4-keto-1,2,2a,3,4,5-hexahydrobenz[cd]indole, 7.7 g. of ammonium acetate and 125 ml. of ethanol. 590 mg. of sodium cyanoborohydride were added and the resulting suspension stirred at ambient temperature for 22 hours. The reaction mixture was then poured over an ice-1N hydrochloric acid mixture and the acidic aqueous layer extracted with chloroform. The aqueous layer was then made basic with 14N aqueous ammonium hydroxide and the alkaline layer extracted several times with chloroform. The chloroform extracts were combined and the combined extracts washed with saturated aqueous sodium chloride and then dried. Evaporation of the chloroform yielded a residue which was shown to be essentially one spot material by TLC. The residue was recrystallized from a mixture of methylene dichloride and ether to yield crystals of 1-benzoyl-4-amino-1,2,2a,3,4,5-hexahydrobenz-[cd]indole melting at 118°-120° C.; yield 825 mg.

Workup

  1. customA reaction mixture was prepared from 2.7 g
  2. extractionthe acidic aqueous layer extracted with chloroform
  3. extractionthe alkaline layer extracted several times with chloroform
  4. washthe combined extracts washed with saturated aqueous sodium chloride
  5. customdried
  6. customEvaporation of the chloroform
  7. customyielded a residue which
  8. customThe residue was recrystallized from a mixture of methylene dichloride and ether

Sources & evidence

ORD record
ord-23a2cdf8d8a64b5780d5358882dd37f9
Source dataset
uspto-grants-1978_08
Patent number
US04110339

Reaction notes

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