Methanol → HCID 69156811, compound

HRID 750219Notes

Reaction equation

HRID 750219 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH:4]=[CH:5][C:6]1[N:7]([CH2:24][C:25]2[CH:33]=[CH:32][C:28]3[O:29][CH2:30][O:31][C:27]=3[CH:26]=2)[C:8](=[O:23])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12](Br)=[CH:11][CH:10]=2.CO>[Ni].C1COCC1>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[N:7]([CH2:24][C:25]2[CH:33]=[CH:32][C:28]3[O:29][CH2:30][O:31][C:27]=3[CH:26]=2)[C:8](=[O:23])[C:9]2[C:14]([C:15]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 887MethanolHCID 69157072HCID 69157072, compound

Product 1

HCID 69156811HCID 69156811, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl]acrylic acid methyl ester (100 mg), Raney-nickel (suitable amount), methanol (2.0 ml) and THF (2.0 ml) was stirred at room temperature under a hydrogen atmosphere for 3 hrs. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1) to give the title compound (55 mg) as a colorless powder.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1)

Sources & evidence

ORD record
ord-b3fca52710a04ea685aee55cad039f49
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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