HCID 23092000, compound → 1-acetylindoline-5-carboxylic acid

HRID 1393674Notes

Reaction equation

HRID 1393674 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15]CC3C=CC=CC=3)=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 23092000HCID 23092000, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 52955471-acetylindoline-5-carboxylic acidYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The benzyl 1-acetyl-1H-indole-5-carboxylate (550 mg) obtained above was suspended in ethanol (9 ml). 10% Palladium on carbon was added thereto, and the mixture was stirred for 16 hours at room temperature in a hydrogen atmosphere. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. Precipitated crystals were collected by filtration, washed with ether and dried under reduced pressure to give the title compound (180 mg, Y.:48%).

Workup

  1. customInsoluble matter was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPrecipitated crystals
  4. filtrationwere collected by filtration
  5. washwashed with ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5a12ce0a24374569b20aba7653d7cafe
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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