m-Chloroperbenzoic acid → Phenyl(5a,6,6a,7a-tetrahydro[1]benzoxireno[4,3,2-cd]indol-4(5H)-yl)methanone

HRID 2420256Notes

Reaction equation

HRID 2420256 reaction equation
[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH:18]=[CH:19][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.ClC1C=CC=C(C(OO)=[O:29])C=1>O.C(Cl)(Cl)Cl>[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH:18]4[O:29][CH:19]4[CH2:20][CH:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 109342511-Benzoyl-1,2,2a,3-tetrahydrobenz[cd]indole

Product 1

HCID 295660Phenyl(5a,6,6a,7a-tetrahydro[1]benzoxireno[4,3,2-cd]indol-4(5H)-yl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent3×

Procedure

A solution was prepared from 2.71 g. of 1-benzoyl-1,2,2a,3-tetrahydrobenz[cd]indole in 100 ml. of chloroform. A second solution containing 2.1 g. of 85% m-chloroperbenzoic acid in 100 ml. of chloroform was added. The reaction mixture was stirred at ambient temperature for 41/4 hours. TLC of an aliquot of the solution indicated that most of the starting material had been comsumed. The reaction mixture was diluted with water and the organic layer washed with 1N aqueous sodium hydroxide, with water and with saturated aqueous sodium chloride. The organic layer was dried and the solvent removed therefrom by evaporation in vacuo. The resulting residue containing 1-benzoyl-4,5-epoxy-1,2,2a,3,4,5-hexahydrobenz[cd]indole formed in the above reaction was dissolved in chloroform and the chloroform solution filtered through florisil. The chloroform was evaporated from the filtrate and the resulting residue crystallized from a mixture of ether and hexane, yielding 1-benzoyl-4,5-epoxy-1,2,2a,3,4,5-hexahydrobenz[cd]indole melting in the range 103°-115° C. (the above procedure is based upon that of Kornfeld et al., J. Am. Chem. Soc., 78, 3101 (1956))

Workup

  1. customA solution was prepared from 2.71 g
  2. additionA second solution containing 2.1 g
  3. washthe organic layer washed with 1N aqueous sodium hydroxide, with water and with saturated aqueous sodium chloride
  4. customThe organic layer was dried
  5. customthe solvent removed
  6. customby evaporation in vacuo
  7. additionThe resulting residue containing 1-benzoyl-4,5-epoxy-1,2,2a,3,4,5-hexahydrobenz[cd]indole
  8. customformed in the above reaction
  9. filtrationthe chloroform solution filtered through florisil
  10. customThe chloroform was evaporated from the filtrate
  11. customthe resulting residue crystallized from a mixture of ether and hexane

Sources & evidence

ORD record
ord-1b11d9bfff3c470d93c515dd7a1a9670
Source dataset
uspto-grants-1978_08
Patent number
US04110339

Reaction notes

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