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

HRID 1504995Notes

Reaction equation

HRID 1504995 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

5

Reactant 3

HCID 962WaterHCID 74193-Aminobenzoic AcidHCID 122703414-Tert-butyl-2-(2-oxo-2-phenylethyl)-cyclohexanone

Product 1

HCID 116031913-(5-Tert-butyl-2-phenyl-4,5,6,7-tetrahydroindol-1-yl)benzoic acidYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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 110 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

  1. temperaturereflux condenser
  2. temperaturewas then heated at 110 C for 3 hr
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customrecrystallized in acetonitrile

Sources & evidence

ORD record
ord-05642a40eefd482190fa46fe6b06715b
Source dataset
uspto-grants-2015_12
Patent number
US09216966B2

Reaction notes

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