HCID 9967439, compound → 1-(3-Carboxy-4-hydroxyphenyl)-2-phenylindole

HRID 1579867Notes

Reaction equation

HRID 1579867 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=[C:12]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([OH:3])=[O:2]>[Pd].C1(C)C(C)=CC=CC=1>[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 9967439HCID 9967439, compound

Product 1

HCID 122703211-(3-Carboxy-4-hydroxyphenyl)-2-phenylindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 3.33 g. (0.01 mole) of 1-(3-carboxy-4-hydroxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole, 4.0 g. of 10% palladium on carbon, and 250 ml. of xylene was heated under reflux with stirring under nitrogen for 3 days, filtered, and concentrated to a solid. Trituration with cyclohexane afforded 2.4 g. (73%) of solid, m.p. 210°-212°. Recrystallization from acetic acid gave colorless crystals, m.p. 213.5°-214.5°.

Workup

  1. additionA mixture of 3.33 g
  2. temperatureunder reflux
  3. filtrationfiltered
  4. concentrationconcentrated to a solid
  5. customTrituration with cyclohexane afforded 2.4 g
  6. customRecrystallization from acetic acid
  7. customgave colorless crystals, m.p. 213.5°-214.5°

Sources & evidence

ORD record
ord-728bd90c54ec400d846fa60fc1d7adc7
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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