6-bromo-2-(3,5-dimethoxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester → 2-(3,5-dimethoxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750138Notes

Reaction equation

HRID 750138 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].[H][H]>CO.[C].[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 2

HCID 691572316-bromo-2-(3,5-dimethoxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 691563952-(3,5-dimethoxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-2-(3,5-dimethoxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (153 mg) in methanol (5 ml) was added palladium carbon (10%, 15 mg), and hydrogen gas was filled. The mixture was stirred at room temperature for 15 hrs. and filtered through celite. The solvent was evaporated under reduced pressure, and the obtained residue was recrystallized from methanol to give the title compound (113 mg, 88%).

Workup

  1. additionwas filled
  2. filtrationand filtered through celite
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was recrystallized from methanol

Sources & evidence

ORD record
ord-fa7c9052377249c0a0e9450c4aff75c0
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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