m-Chloroperbenzoic acid → 6-bromo-2-(4-methanesulfinylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750294Notes

Reaction equation

HRID 750294 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][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:21])=[CH:10][CH:9]=2)=[O:4].ClC1C=CC=C(C(OO)=[O:40])C=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([S:30]([CH3:31])=[O:40])=[CH:28][CH:29]=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:21])=[CH:10][CH:9]=2)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69155526HCID 69155526, compound

Product 1

HCID 691569256-bromo-2-(4-methanesulfinylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (6.7 ml) of 6-bromo-2-(4-methylsulfanylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (334 mg) in dichloromethane was added m-chloro perbenzoic acid (200 mg) at 0° C. with stirring, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was washed with 1N sodium hydroxide and water, and the organic layer was dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1-1/4) to give the title compound (160 mg) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. washThe reaction mixture was washed with 1N sodium hydroxide and water
  3. customthe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1-1/4)

Sources & evidence

ORD record
ord-c84881d50c584d0cbe93fa77394cf6c8
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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