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Ammonium Chloride → 3-acetyl-2-(4-acetylbenzyl)-6-bromo-4-phenyl-2H-isoquinolin-1-one

HRID 750317
Notes
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Reaction equation

HRID 750317 reaction equation
[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:34]=[CH:33][C:26]([C:27](N(OC)C)=[O:28])=[CH:25][CH:24]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:10]([Br:20])=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[CH3:35][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:34]=[CH:33][C:26]([C:27](=[O:28])[CH3:35])=[CH:25][CH:24]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][C:10]([Br:20])=[CH:9][CH:8]=2)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 865995664-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 230609443-acetyl-2-(4-acetylbenzyl)-6-bromo-4-phenyl-2H-isoquinolin-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 4-(3-acetyl-6-bromo-1-oxo-4-phenyl-1H-isoquinolin-2-ylmethyl)-N-methoxy-N-methylbenzamide (330 mg) in tetrahydrofuran (10 ml) was added methyl magnesium bromide (3M tetrahydrofuran solution, 0.64 ml) under ice-cooling and the mixture was stirred for 2 hrs. under ice-cooling. The reaction solution was poured into saturated aqueous ammonium chloride solution, extracted with ethyl acetate, washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→7/3) to give the title compound (259 mg, 87%).

Workup

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=19/1→7/3)

Sources & evidence

ORD record
ord-61e5c7f63c3b46bba2edd33cf84e3f11
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07402595B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes