Water → 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril

HRID 1770135Notes

Reaction equation

HRID 1770135 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[H-].[Na+].Cl[CH2:16][CH:17]([OH:28])[CH2:18][N:19]([CH3:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[CH3:27][N:19]([CH2:18][CH:17]([OH:28])[CH2:16][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2)[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1770652,6-DihydroxyquinolineHCID 147198711-chloro-2-hydroxy-3-(N-methyl-N-benzylamino)propane

Product 1

HCID 103597756-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyrilYield 22.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxycarbostyril (1.6 g) and sodium hydride (50% oily) (1 g) in dimethylformamide (30 ml), 1-chloro-2-hydroxy-3-(N-methyl-N-benzylamino)propane (2.2 g) is added dropwise at room temperature. After the addition, the mixture is heated with stirring at 70°-80° C. for 3 hours. The reaction mixture is poured into water and extracted with chloroform, and the extract is dried over magnesium sulfate. Chloroform is distilled off and the resulting residue is purified by silica gel column chromatography (solvent; methanol:chloroform=1:100-1:25) and recrystallized from ethanol to give 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril (0.76 g), as white powder, m.p. 129°-132° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is heated
  3. extractionextracted with chloroform
  4. dry with materialthe extract is dried over magnesium sulfate
  5. distillationChloroform is distilled off
  6. customthe resulting residue is purified by silica gel column chromatography (solvent; methanol:chloroform=1:100-1:25)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-440b0e3c66944ba3ad85353db6b347cd
Source dataset
uspto-grants-1995_01
Patent number
US05385914

Reaction notes

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