5-Aminosalicylic Acid → 1-(3-Carboxy-4-hydroxyphenyl)-5-methyl-2-phenyl-4,5,6,7-tetrahydroindole

HRID 1579893Notes

Reaction equation

HRID 1579893 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=O)[CH:4]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH2:3]1.[NH2:18][C:19]1[CH:27]=[C:23]([C:24]([OH:26])=[O:25])[C:22]([OH:28])=[CH:21][CH:20]=1>C(O)(=O)C>[C:24]([C:23]1[CH:27]=[C:19]([N:18]2[C:5]3[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][C:4]=3[CH:9]=[C:10]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:20]=[CH:21][C:22]=1[OH:28])([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 122703404-Methyl-2-(2-oxo-2-phenylethyl)cyclohexanone

Product 1

HCID 122703101-(3-Carboxy-4-hydroxyphenyl)-5-methyl-2-phenyl-4,5,6,7-tetrahydroindole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

a solution of 50 g. (0.22 mole) of 4-methyl-2-phenacylcyclohexanone, 33.7 g. (0.22 mole) of 5-aminosalicylic acid, and 257 ml. of glacial acetic acid was heated under reflux for 3 hours, cooled and filtered. The collected solid was washed with water and recrystallized from acetonitrile to provide 43.3 g. (57%) of yellow crystals, m.p. 213°-215°.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe collected solid was washed with water
  5. customrecrystallized from acetonitrile
  6. customto provide 43.3 g

Sources & evidence

ORD record
ord-fb23a48c86634586b2e838f2c2738133
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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