Dimethylformamide → HCID 68780406, compound

HRID 2266426Notes

Reaction equation

HRID 2266426 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]2[C:6]=1[C:7]([CH3:25])=[C:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:9](=[O:16])[NH:10]2.Br[CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]2[C:6]=1[C:7]([CH3:25])=[C:8]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:9]([O:16][CH2:28][CH3:29])=[N:10]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 68605729HCID 68605729, compound

Product 1

HCID 68780406HCID 68780406, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of [3-(4-chlorobenzyl)-4,7-dimethyl-2-oxo-1,2-dihydroquinolin-5-yl]acetic acid methyl ester (1.0 g), bromoethane (0.24 mL), potassium carbonate (1.1 g) and N,N-dimethylformamide (10 mL) was heated at 40° C. for 17 hours. The mixture was diluted with ethyl acetate and washed with water and saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of ethyl acetate and dichloromethane (0:1 to 1:5 by volume) gave title compound as a gum, 0.28 g.

Workup

  1. washwashed with water and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  4. washeluting with a mixture of ethyl acetate and dichloromethane (0:1 to 1:5 by volume)

Sources & evidence

ORD record
ord-98494efdd5af414dacc1ba3b5a9c71cb
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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