Water → 6,7-dimethoxy-1-(4-methoxybenzyl)-4(1H)-quinolone

HRID 1090131Notes

Reaction equation

HRID 1090131 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=[O:15].[H-].[Na+].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]([CH2:24][C:23]1[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)[CH:8]=[CH:7][C:6]2=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 4596116,7-Dimethoxy-4-hydroxyquinoline

Product 1

HCID 156752506,7-dimethoxy-1-(4-methoxybenzyl)-4(1H)-quinolone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6,7-Dimethoxy-4(1H)-quinolone (0.5 g) was dissolved in dimethylformamide (10 ml). 60% Sodium hydride (130 mg) and 4-methoxybenzyl bromide (0.42 ml) were added to the solution, and the mixture was stirred at room temperature for 15 hours. Water was added to the mixture, and extraction was conducted with ethyl acetate. The extract was washed with water and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wako Gel C-200, 30 g). Elution with a mixed solvent of chloroform (90 parts) and methanol (10 parts) gave 6,7-dimethoxy-1-(4-methoxybenzyl)-4(1H)-quinolone (compound 17, 0.39 g).

Workup

  1. washThe extract was washed with water
  2. dry with materialdried over sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 30 g)
  5. washElution with a mixed solvent of chloroform (90 parts) and methanol (10 parts)

Sources & evidence

ORD record
ord-7be9468d60144824b5004df02e4a7276
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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