3-Aminobenzoic Acid → 1-(3-Carboxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

HRID 1579857Notes

Reaction equation

HRID 1579857 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.[NH2:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=[O:22]>C(O)(=O)C>[C:21]([C:20]1[CH:19]=[C:18]([N:17]2[C:11]3[CH2:12][CH2:13][CH2:14][CH2:15][C:10]=3[CH:1]=[C:2]2[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:26]=[CH:25][CH:24]=1)([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 105128992-(2-Oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 122702731-(3-Carboxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 10.8 g. (0.05 mole) of 2-phenacylcyclohexanone, 6.85 g. (0.05 mole) of m-aminobenzoic acid and 30 ml. of glacial acetic acid was heated under reflux for 6 hours, cooled and filtered. The filter cake was washed with water and recrystallized from ethanol to provide 5.7 g. (36%) of crystals, m.p. 191°-193°.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. customrecrystallized from ethanol
  6. customto provide 5.7 g

Sources & evidence

ORD record
ord-b1fcd584fbe64fe1b87ff6884de54069
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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