Dimethylformamide → Allyl 2-(2-chlorophenyl)-4-quinolone-8-carboxylate

HRID 986249Notes

Reaction equation

HRID 986249 reaction equation
[K].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:18][C:17](=[O:19])[C:16]2[C:11](=[C:12]([C:20]([OH:22])=[O:21])[CH:13]=[CH:14][CH:15]=2)[N:10]=1.[CH2:23](Br)[CH:24]=[CH2:25].CN(C)C=O>O>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH2:18][C:17](=[O:19])[C:16]2[C:11](=[C:12]([C:20]([O:22][CH2:25][CH:24]=[CH2:23])=[O:21])[CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 5462222PotassiumHCID 704331432-(2-Chlorophenyl)-4-quinolone-8-carboxylic acid

Product 1

HCID 70432932Allyl 2-(2-chlorophenyl)-4-quinolone-8-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7 grams of the potassium salt of 2-(2-chlorophenyl)-4-quinolone-8-carboxylic acid were added 2 ml of allyl bromide and 200 ml of dimethyl formamide, the mixture was stirred at 70° to 80° C. for 6 hours, and poured into water. The mixture was extracted with chloroform, the solvent was removed from the extract, and the residue was recrystallized from acetone to give 5.6 grams of the title compound, pale yellow needles, melting point 121° C.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. customthe solvent was removed from the extract
  3. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-b4fb6c5930a346d5bfa558a78705d858
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

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