HCID 19363444, compound → HCID 19363528, compound

HRID 850501Notes

Reaction equation

HRID 850501 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:33][CH3:34])[C:23]=3[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:18]2=[O:35])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:33][CH3:34])[C:23]=3[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:18]2=[O:35])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 19363444HCID 19363444, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363528HCID 19363528, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-[2-(4-Benzyloxyphenyl)ethyl]-6-methoxy-5-pentyloxy-2H-isoquinolin-1-one (1.21 g, 2.6 mmol, 1.0 eq) was dissolved in ethyl acetate (12 ml), and 10% palladium-carbon catalyst (300 mg, water content 50%) was added. The mixture was stirred in a stream of hydrogen for 4 hours. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1-ethyl acetate) to give 2-[2-(4-hydroxyphenyl)ethyl]-6-methoxy-5-pentyloxy-2H-isoquinolin-1-one (681.8 mg, 68.7%) as colorless crystals.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1-ethyl acetate)

Sources & evidence

ORD record
ord-a5d3806319514e1cb082cd5ca492af22
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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