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Ammonium Chloride → 3-acetyl-6-bromo-2-[4-(1-hydroxy-1-methylethyl)benzyl]-4-phenyl-2H-isoquinolin-1-one

HRID 750324
Notes
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Reaction equation

HRID 750324 reaction equation
[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[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].[CH3:32][Mg]Br.[Cl-].[NH4+]>C1COCC1>[C:1]([C:4]1[N:5]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([OH:31])([CH3:32])[CH3:30])=[CH:27][CH:28]=2)[C:6](=[O:21])[C:7]2[C:12]([C:13]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=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 230609443-acetyl-2-(4-acetylbenzyl)-6-bromo-4-phenyl-2H-isoquinolin-1-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 230609083-acetyl-6-bromo-2-[4-(1-hydroxy-1-methylethyl)benzyl]-4-phenyl-2H-isoquinolin-1-oneYield 83%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 3-acetyl-2-(4-acetylbenzyl)-6-bromo-4-phenyl-2H-isoquinolin-1-one (297 mg) in THF (10 ml) was added methyl magnesium bromide (1M tetrahydrofuran solution, 1.89 ml) under ice-cooling and the mixture was stirred under ice-cooling for 1 hr. The reaction solution was poured into saturated aqueous ammonium chloride solution, extracted with ethyl acetate, washed with 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=9/1→3/2) to give the title compound (258 mg, 83%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. extractionextracted with ethyl acetate
  4. washwashed with 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=9/1→3/2)

Sources & evidence

ORD record
ord-57840030b115461eb9cb1d84d5e654a4
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