HCID 12270311, compound → HCID 12270322, compound

HRID 1579889Notes

Reaction equation

HRID 1579889 reaction equation
[C:1]([CH:5]1[CH2:13][CH2:12][C:11]2[N:10]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]([OH:23])=[O:22])[CH:15]=3)[C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:8][C:7]=2[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([C:21]([OH:23])=[O:22])[CH:15]=1)[C:9]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 12270311HCID 12270311, compound

Product 1

HCID 12270322HCID 12270322, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 16 g. (0.041 mole) of 5-(t-butyl)-1-(3-carboxy-4-hydroxyphenyl)-2-phenyl-4,5,6,7-tetrahydroindole, 8 g. of 10% palladium on carbon, and 1.6 l. of xylene was heated under reflux under nitrogen for 23 hours and filtered. The filtrate was concentrated to 400 ml., cooled and filtered to provide 13.0 g. (82%) of crystals, m.p. 275°-276°. Recrystallization from acetonitrile gave crystals, m.p. 271°-273°.

Workup

  1. additionA mixture of 16 g
  2. temperatureunder reflux under nitrogen for 23 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to 400 ml
  5. temperature, cooled
  6. filtrationfiltered
  7. customto provide 13.0 g
  8. customRecrystallization from acetonitrile
  9. customgave crystals, m.p. 271°-273°

Sources & evidence

ORD record
ord-cd9401460f5244bebc4741c2969c91b4
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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