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

HRID 1684582Notes

Reaction equation

HRID 1684582 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e46565d5316546d1a497871a7a1ecb90
Source dataset
uspto-grants-1997_06
Patent number
US05641788

Reaction notes

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