HCID 21548669, compound → 35571-36-9

HRID 1605097Notes

Reaction equation

HRID 1605097 reaction equation
[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([OH:24])=[O:23])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([O:25]C(=O)C1C=CC=CC=1)[CH:14]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(OCC)(=O)C>[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([OH:24])=[O:23])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([OH:25])[CH:14]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 21548669HCID 21548669, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 2154864535571-36-9

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8.1 g. of 9-benzoyl-6-benzoyloxy-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid in 250 ml. of ethyl acetate over 1.5 g. of 10 percent palladium-on-charcoal was subjected to a hydrogen atmosphere at about 40 psig while being heated with a heat lamp. The reaction was stopped when a theoretical amount of hydrogen had been adsorbed (1 hour) and the resulting cooled mixture was filtered and evaporated to dryness under reduced pressure. The residue was crystallized from acetone-n-hexane to yield 4.1 g. of the title compound; m.p. 224°-227°C.

Workup

  1. temperaturewhile being heated with a heat lamp
  2. custom(1 hour)
  3. temperaturethe resulting cooled mixture
  4. filtrationwas filtered
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was crystallized from acetone-n-hexane
  7. customto yield 4.1 g

Sources & evidence

ORD record
ord-c672d48194da430ba9bbcd0bb0ce761e
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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