HCID 19363444, compound → HCID 19363271, compound

HRID 850499Notes

Reaction equation

HRID 850499 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]>[OH-].[Pd+2].[OH-].[C].C(O)(=O)C>[CH3:34][O:33][C:22]1[C:23]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:24]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:35])[N:17]([CH2:16][CH2:15][CH:12]1[CH2:13][CH2:14][C:9](=[O:8])[CH2:10][CH2:11]1)[CH2:26][CH2:25]2

Participants

5

Reactant 2

HCID 19363444HCID 19363444, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19363271HCID 19363271, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

10% Palladium hydroxide-carbon catalyst (300 mg, water content 50%) was added to a solution of 2-[2-(4-benzyloxyphenyl)ethyl]-6-methoxy-5-pentyloxy-2H-isoquinolin-1-one (1.18 g, 2.5 mmol, 1.0 eq) in acetic acid (20 ml), and the mixture was stirred with heating in a stream of hydrogen for 4 hours at 60-70° C. at 3 kgf/cm2. 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=4/1) to give 6-methoxy-2-[2-(4-oxocyclohexyl)ethyl]-5-pentyloxy-3,4-dihydro-2H-isoquinolin-1-one (800 mg, 82.6%) as a pale-yellow oil.

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=4/1)

Sources & evidence

ORD record
ord-fba1ff3118c24b498c9499e48378965f
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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