3-Aminobenzoic Acid → 3-(5-methyl-2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzoic acid

HRID 2064556Notes

Reaction equation

HRID 2064556 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=O)[CH:4]([CH2:9][C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22]([OH:24])=[O:23]>>[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]2[N:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=3)[C:22]([OH:24])=[O:23])[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][C:4]=2[CH2:3]1

Participants

3

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 122703404-Methyl-2-(2-oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 592144733-(5-methyl-2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzoic acidYield 69%

Procedure

Following the general methods as outlined under Intermediate 13, starting from 4-methyl-2-(2-oxo-2-phenylethyl)cyclohexanone and 3-aminobenzoic acid, the title compound was isolated in 69% yield (98% purity by HPLC). MS(ESI+): 332.4; MS(ESI−): 330.6.

Sources & evidence

ORD record
ord-d080ced523e14ac29a823b3e84e19d52
Source dataset
uspto-grants-2012_10
Patent number
US08288432B2

Reaction notes

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