alpha-Ethyl-beta-oxobenzenepropanoic acid → 1-Benzoyl-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

HRID 1637251Notes

Reaction equation

HRID 1637251 reaction equation
Cl.C1(NN)C=CC=CC=1.[C:10]1([C:16]2[NH:17][C:18]3[C:23]([C:24]=2[CH2:25][CH2:26][C:27](O)=[O:28])=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:30](C(CC)C(O)=O)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(O)(=O)C>[C:30]([N:17]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27](=[O:28])[CH2:26][CH2:25][CH:24]([C:23]=23)[CH:16]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 21651867alpha-Ethyl-beta-oxobenzenepropanoic acidHCID 703070592-phenylindole-3-propionic acid Phenylhydrazine hydrochloride

Product 1

HCID 193483011-Benzoyl-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-oneYield 160.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(Step 1) Synthesis of 2-phenylindole-3-propionic acid Phenylhydrazine hydrochloride (50 g) and benzoylbutyric acid (55.4 g) were suspended in acetic acid (500 ml), followed by heating to reflux for 1.5 hours. After allowing the suspension to cool, the insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. Water was added to the residue, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous solution of sodium chloride, and thereafter dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized from an ether/hexane mixed solvent, followed by washing with a methylene chloride/hexane mixed solvent to yield 69 g (90%) of the titled compound as pale brown crystals.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. filtrationthe insoluble matter was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with water and saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was crystallized from an ether/hexane mixed solvent
  12. washby washing with a methylene chloride/hexane mixed solvent

Sources & evidence

ORD record
ord-18e26b6b07b9483a83da1ce235858637
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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