4-Aminophenol → HCID 21446102, compound

HRID 597712Notes

Reaction equation

HRID 597712 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([OH:11])=O.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.O>C1(C)C(C)=CC=CC=1>[OH:25][C:22]1[CH:23]=[CH:24][C:19]([N:18]2[CH:2]3[C:3]([CH2:4][CH2:5][CH2:6][CH2:7]3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]2=[O:11])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 962WaterHCID 13284199HCID 13284199, compound

Product 1

HCID 21446102HCID 21446102, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

92.8 g of 2-(2-oxo-cyclohexyl)-2-phenyl acetic acid and 44 g of 4-aminophenol in 800 cm3 of xylene were stirred and heated under reflux, as indicated in Example 1a), until the water formed in the reaction has been totally eliminated. This took 2 hours (volume collected: 14.2 cm3 ; theoretical: 14.4 cm3). After the distillation of 400 cm3 of solvent, the residue was cooled. The precipitate produced was collected and recrystallized from methylcellosolve to give 100 g (82%) of 1-(4-hydroxyphenyl)-2-oxo-3-phenyl-2,4,5,6,7,7a-hexahydro-indole (m.p. 241° C).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customformed in the reaction
  4. customThis took 2 hours (volume collected: 14.2 cm3 ; theoretical: 14.4 cm3)
  5. distillationAfter the distillation of 400 cm3 of solvent
  6. temperaturethe residue was cooled
  7. customThe precipitate produced
  8. customwas collected
  9. customrecrystallized from methylcellosolve

Sources & evidence

ORD record
ord-e2a25d5670434c6792a5f11fb5df1fa6
Source dataset
uspto-grants-1977_03
Patent number
US04015002

Reaction notes

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