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

HRID 1579859Notes

Reaction equation

HRID 1579859 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:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1>C(O)(=O)C>[C:22]([C:21]1[CH:25]=[CH:26][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:19][CH:20]=1)([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 105128992-(2-Oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 66233704-(2-phenyl-4,5,6,7-tetrahydro-1H-indol-1-yl)benzoic acid

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 p-aminobenzoic acid and 30 ml. of glacial acetic acid was heated under reflux for 5 hours and cooled. The solid which separated was collected and recrystallized from ethanol to provide 5.85 g. (37%) of pale yellow crystals, m.p. 244°-246°.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperaturecooled
  3. customThe solid which separated
  4. customwas collected
  5. customrecrystallized from ethanol
  6. customto provide 5.85 g

Sources & evidence

ORD record
ord-89efef959bb24191b0390427ec7072a7
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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