Acetic Acid → HCID 15428721, compound

HRID 1585217Notes

Reaction equation

HRID 1585217 reaction equation
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>[C].[Pd].[H][H]>[C:1]([N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 14435469HCID 14435469, compound

Product 1

HCID 15428721HCID 15428721, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of 3.0 g of 1-benzoyl-3-phenylindole, 0.33 g of 10% palladium-carbon catalyst, and 60 ml of acetic acid was stirred in hydrogen for six hours under the conditions of 60° C. and normal pressure, cooled, then filtered to remove the catalyst, and distilled to expel the acetic acid. The residue was alkalinized by addition of an aqueous sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then distilled to expel the ethyl acetate and obtain 2.94 g of 1-benzoyl-3-phenylindoline (97.4%) having a melting point of 127-129° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customto remove the catalyst
  4. distillationdistilled
  5. additionThe residue was alkalinized by addition of an aqueous sodium hydroxide solution
  6. extractionextracted with ethyl acetate
  7. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  8. distillationdistilled

Sources & evidence

ORD record
ord-8cb13cb81dae41228c2aa4613d70ff1d
Source dataset
uspto-grants-1999_08
Patent number
US05936098

Reaction notes

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