Hydrochloric Acid → HCID 22414846, compound

HRID 1721422Notes

Reaction equation

HRID 1721422 reaction equation
C([N:8]1[C:16]2[C:11](=[C:12]([OH:18])[CH:13]=[CH:14][C:15]=2[CH3:17])[C:10]([CH3:20])([CH3:19])[C:9]1=[O:21])C1C=CC=CC=1.[H][H].Cl>C(O)(=O)C.[C].[Pd].C(OCC)(=O)C>[OH:18][C:12]1[CH:13]=[CH:14][C:15]([CH3:17])=[C:16]2[C:11]=1[C:10]([CH3:20])([CH3:19])[C:9](=[O:21])[NH:8]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 22414877HCID 22414877, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22414846HCID 22414846, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

41.0 g (146 mmol) of 1-benzyl-2,3-dihydro-4-hydroxy-3,3,7-trimethyl-1H-indol-2-one was dissolved in 11 of acetic acid. After the addition of 82 g of a 10% palladium-carbon catalyst, the reaction atmosphere was replaced with hydrogen and 40 ml (160 mmol) of 4N hydrogen chloride solution in ethyl acetate was added, following which the mixture was stirred for 2.5 hours over a water bath at 80° C. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue obtained was purified by column chromatography (silica gel, 4:1 mixture of chloroform and methanol) and recrystallized (ether) to obtain 27.58 g (yield, 98.9%) of colorless prisms of the title compound.

Workup

  1. customthe reaction atmosphere
  2. additionwas added
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 4:1 mixture of chloroform and methanol)
  7. customrecrystallized (ether)
  8. customto obtain

Sources & evidence

ORD record
ord-40e9e72e7b2c459eb7d6e5a25234a755
Source dataset
uspto-grants-1996_04
Patent number
US05510366

Reaction notes

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