Water → 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-3-(1-hydroxyethyl)-6,7-dimethoxyquinoline

HRID 1684582노트

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HRID 1684582 반응식
[C:1]([C:4]1[C:5]([CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[CH:11][C:10]([O:24][CH3:25])=[C:9]([O:26][CH3:27])[CH:8]=2)(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:32]([N:29]([CH2:28][C:5]1[C:4]([CH:1]([OH:3])[CH3:2])=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[C:12]2[C:7](=[CH:8][C:9]([O:26][CH3:27])=[C:10]([O:24][CH3:25])[CH:11]=2)[N:6]=1)[CH2:30][CH3:31])[CH3:33]

참가 물질

5

반응물 3

HCID 962WaterHCID 98900803-acetyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinolineHCID 21226445Aluminium lithium hydride

생성물 1

HCID 540526452-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-3-(1-hydroxyethyl)-6,7-dimethoxyquinoline수율 45.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-Acetyl-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (0.5 g) was added to an ice-cooled suspension of lithium aluminum hydride (0.045 g) in tetrahydrofuran (10 ml). The mixture was stirred at room temperature for 20 minutes. Then, water (0.3 ml) was added, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethanol (20:1, v/v) gave 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-3-(1-hydroxyethyl)-6,7-dimethoxyquinoline (0.23 g, 45%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 144°-145° C.

후처리

  1. temperaturecooled
  2. filtrationthe insoluble material was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washThe fractions eluted with chloroform-ethanol (20:1

출처 및 근거

ORD 기록
ord-e46565d5316546d1a497871a7a1ecb90
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05641788

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