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

HRID 750317
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HRID 750317 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-61e5c7f63c3b46bba2edd33cf84e3f11
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07402595B2

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