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

HRID 917893Notes

Reaction equation

HRID 917893 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C(O)(=O)C>C(O)(C)C>[CH3:17][O:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:2]3[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=3[CH:8]=[C:9]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7732P-AnisidineHCID 105128992-(2-Oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 135225381-(4-Methoxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Following a procedure similar to that of Example 1C but using 64.9 g. of 2-(2-oxocyclohexyl)acetophenone and 37 g. of 4-methoxyaniline in 180 ml. glacial acetic acid there was obtained 80.9 g. of 1-(4-methoxyphenol)-2-phenol-4,5,6,7-tetrahydroindole; m.p. 132°-133°C. (isopropyl alcohol).

Sources & evidence

ORD record
ord-e308877d423548a48c23363ebbd1ff24
Source dataset
uspto-grants-1976_07
Patent number
US03968121

Reaction notes

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