Acetic Acid → 1-(2-Methoxycarbonylphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

HRID 1579858Notes

Reaction equation

HRID 1579858 reaction equation
[CH2:1]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[C:17]([O:26][CH3:27])(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[NH2:20].C(O)(=O)C>O>[CH3:27][O:26][C:17]([C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[N:20]1[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=2[CH:1]=[C:2]1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8635Methyl AnthranilateHCID 105128992-(2-Oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 215696221-(2-Methoxycarbonylphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10.8 g. (0.05 mole) of 2-phenacylcyclohexanone, 7.55 g. (0.05 mole) of methyl anthranilate, and 30 ml. of glacial acetic acid was heated under reflux for 7 hours, cooled, and diluted with water. The layers were separated, and the aqueous phase was extracted with ether. The combined organic phase was washed with sodium bicarbonate solution, dried over sodium sulfate, and concentrated to an oil. Chromatography on silica gel with toluene as the eluent gave 2.91 g. (18%) of a yellow oil.

Workup

  1. temperatureunder reflux for 7 hours
  2. temperaturecooled
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ether
  5. washThe combined organic phase was washed with sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to an oil
  8. customChromatography on silica gel with toluene as the eluent gave 2.91 g

Sources & evidence

ORD record
ord-5b7885ef39ff4343a380fc5e107c5f6e
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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