Water → 3-(5-Tert-butyl-2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acid

HRID 574137Notes

Reaction equation

[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH:7]([CH2:12][C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26].O>C(O)(=O)C>[C:1]([CH:5]1[CH2:10][CH2:9][C:8]2[N:21]([C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=[O:26])[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][C:7]=2[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 11 °C

Procedure

A solution of 4-tert-butyl-2-(2-oxo-2-phenylethyl)-cyclohexanone (0.219 gm) in glacial acetic acid (3.0 mL) in a 25-mL round-bottomed flask, under nitrogen, was fitted with a heating mantle and reflux condenser. To this solution was added 3-aminobenzoic acid (0.138 gm), which was then heated at 11° C. for 3 hr. The solution was cooled to ambient temperature, 8 mL water was added, and the suspension was stirred 18 hr under nitrogen. The solid was filtered, washed with water, and recrystallized in acetonitrile to provide 0.123 gm of the pure product.

Workup

temperaturereflux condenser
temperatureThe solution was cooled to ambient temperature
filtrationThe solid was filtered
washwashed with water
customrecrystallized in acetonitrile

Sources & evidence

ORD record: ord-050afd1be5e64922abb0a1c7749ce41e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034871B2

Reaction notes

Loading…