Sodium Bicarbonate → Acetic acid 2-(6-methyl-pyridin-2-yl)-2-oxo-1-quinolin-6-yl-ethyl ester

HRID 917678Notes

Reaction equation

HRID 917678 reaction equation
Br.Br[CH:3]([C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][CH:17]=[CH:16]2)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)=[O:5].[C:23]([O-:26])(=[O:25])[CH3:24].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:12][C:8]1[N:7]=[C:6]([C:4](=[O:5])[CH:3]([O:26][C:23](=[O:25])[CH3:24])[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 865927622-Bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone hydrobromide

Product 1

HCID 68883979Acetic acid 2-(6-methyl-pyridin-2-yl)-2-oxo-1-quinolin-6-yl-ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of of 2-bromo-1-(6-methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone hydrobromide (94 mg, 0.36 mmol), and potassium acetate (70 mg, 0.72 mmol, 2 equiv) in dimethylformamide (2 mL) is heated to 60° C. for 1 hour. The resulting reaction mixture is cooled to ambient temperature, treated with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The organics are washed with brine, dried with magnesium sulfate and concentrated in vacuo to provide acetic acid 2-(6-methyl-pyridin-2-yl)-2-oxo-1-quinolin-6-yl-ethyl ester.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organics are washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15f10d192185450cb528d7cc61132003
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

Loading…