Hydrochloric Acid → 2-Phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

HRID 1637256Notes

Reaction equation

HRID 1637256 reaction equation
C([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18](=[O:21])[CH2:19][CH2:20][CH:11]([C:12]=23)[CH:10]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)C1C=CC=CC=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[C:22]1([CH:10]2[CH:11]3[CH2:20][CH2:19][C:18](=[O:21])[C:13]4[C:12]3=[C:17]([CH:16]=[CH:15][CH:14]=4)[NH:9]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 193483011-Benzoyl-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

Product 1

HCID 193482872-Phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-oneYield 111.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A portion (4.25 g) of the compound obtained in Example 1 was dissolved in ethanol (40 ml). To the solution was added conc. hydrochloric acid (40 ml) and the resulting mixture was heated to reflux for 2 hours. After allowing to cool, the mixture was diluted with water, adjusted to pH 9 with potassium carbonate and extracted three times with ethyl acetate. The organic layers were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure and the residue was crystallized from an ether/hexane mixed solvent to yield 3.33 g (92%) of the titled compound as crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureto cool
  4. extractionextracted three times with ethyl acetate
  5. washwashed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customthe residue was crystallized from an ether/hexane mixed solvent

Sources & evidence

ORD record
ord-0fe79847ea854760944a0e9f26b3988d
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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