Fendosal → HCID 12270320, compound

HRID 1579883Notes

Reaction equation

HRID 1579883 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:11]2[C:19]3[CH2:18][CH2:17][C:16]4[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=4[C:14]=3[CH:13]=[C:12]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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[CH:18]=[CH:17][C:16]4[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=4[C:14]=3[CH:13]=[C:12]2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:8][C:9]=1[OH:10])([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 40821Fendosal

Product 1

HCID 12270320HCID 12270320, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A mixture of 7.6 g. (0.02 mole) of 3-(3-carboxy-4-hydroxyphenyl)-4,5-dihydro-2-phenylbenz[e]indole, 9.1 g. of 10% palladium on carbon, and 350 ml. of xylene was heated under reflux with stirring under nitrogen for 24 hours and then filtered. The filtrate was concentrated to 135 ml. and cooled. The solid which separated was collected and recrystallized from xylene to provide 3.6 g. (48%) of yellow crystals, m.p. 241.5°-242.5°.

Workup

  1. additionA mixture of 7.6 g
  2. temperatureunder reflux
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to 135 ml
  5. temperatureand cooled
  6. customThe solid which separated
  7. customwas collected
  8. customrecrystallized from xylene
  9. customto provide 3.6 g

Sources & evidence

ORD record
ord-e70e6a62382a4ca7a170943d8a9f7d16
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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