Dimethylformamide → HCID 54112822, compound

Reaction equation

[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:22])[C:7]([C:19]([OH:21])=[O:20])=[CH:8][N:9]3[CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:4][C:3]=2[O:2]1.CN(C)C=O.[CH3:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33]Cl)=[O:31]>C(N(CC)CC)C>[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=[O:22])[C:7]([C:19]([O:21][CH2:33][O:32][C:30](=[O:31])[C:29]([CH3:36])([CH3:35])[CH3:28])=[O:20])=[CH:8][N:9]3[CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:4][C:3]=2[O:2]1

Participants

Procedure

To a mixture of 2.6 g. 6,7-methylenedioxy-1-(2,2,2-trifluoroethyl)-4(1H)-quinolone-3-carboxylic acid and 35 ml. of dimethyl formamide was added 1.4 g. of triethylamine. The mixture was warmed to 55° and kept there for 1/2 hour. 2.8 g. of chloromethyl trimethylacetate was then added and the resulting mixture was stirred at 55° for 5 hours. The cooled solution was diluted with 150 ml. of ethyl acetate and washed with water. The ethyl acetate solution was dried over magnesium sulfate and concentrated. The solid residue, 6,7-methylenedioxy-1-(2,2,2-trifluoroethyl)-4(1H)-quinolone-3-carboxylic acid, trimethylacetoxymethyl ester, was recrystallized from CH2C12 -ether mixture; m.p. 190°-1° .