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Water → 1-(4-Methylphenyl)-5-hydroxymethylisoquinoline

HRID 1156901
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HRID 1156901 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([C:18](OCC)=[O:19])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18][OH:19])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 128518431-(4-Methylphenyl)-5-ethoxycarbonylisoquinolineHCID 21226445Aluminium lithium hydride

생성물 1

HCID 128518441-(4-Methylphenyl)-5-hydroxymethylisoquinoline수율 60.4%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

1-(4-Methylphenyl)-5-ethoxycarbonylisoquinoline (14.5 g) was dissolved in 200 ml of anhydrous tetrahydrofuran, and with stirring under cooling, lithium aluminum hydride (suspended in 100 ml of tetrahydrofuran) was added dropwise. The mixture was stirred at room temperature for 1 hour. Water and a 20% aqueous solution of sodium hydroxide were added to the reaction mixture, and the mixture was stirred for 30 minutes. The reaction mixture was filtered through Celite. The filtrate was concentrated, and the residue was recrystallized from benzene to afford 7.5 g of 1-(4-methylphenyl)-5-hydroxymethylisoquinoline as colorless needles.

후처리

  1. temperatureunder cooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. stirringthe mixture was stirred for 30 minutes
  4. filtrationThe reaction mixture was filtered through Celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue was recrystallized from benzene

출처 및 근거

ORD 기록
ord-0b359797df1641de94439a92d334aaa1
출처 데이터셋
uspto-grants-1982_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04337256

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