Water → Ethyl 6-acetoxymethyl-3-methylquinoline-2-carboxylate

HRID 1604547Notes

Reaction equation

HRID 1604547 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]([CH3:18])=[CH:6]2.[C:19]([O-:22])(=[O:21])[CH3:20].[Na+].O>CN(C)C=O>[C:19]([O:22][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]([CH3:18])=[CH:6]2)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 19603253Ethyl 6-bromomethyl-3-methylquinoline-2-carboxylate

Product 1

HCID 19603481Ethyl 6-acetoxymethyl-3-methylquinoline-2-carboxylateYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 6-bromomethyl-3-methylquinoline-2-carboxylate (700 mg) in dimethylformamide (7 ml) was added sodium acetate (373 mg) at ambient temperature, and the mixture was stirred for 24 hours at the same temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:2, V/V) to give ethyl 6-acetoxymethyl-3-methylquinoline-2-carboxylate (452 mg) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:2, V/V)

Sources & evidence

ORD record
ord-b4d1a192c5d64822a47b809d92921fd8
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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