Clonixin → HCID 12673425, Verbindung

Reaktionsgleichung

[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1.[C:19]([O:25][CH2:26]Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>CC(C)=O.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:15]=[CH:16][CH:17]=1)[NH:5][C:6]1[C:11]([C:12]([O:14][CH2:26][O:25][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1

Komponenten

Versuchsvorschrift

To a stirred mixture of 2-(3'-chloro-2'-methylanilino)-pyridine-3-carboxylic acid (26.3 g) in 400 ml of acetone, triethylamine (20.5 ml) was added. Thereafter pivaloyloxymethyl chloride (15 ml) was poured into the mixture and then it was refluxed 4 hours. Subsequently, the reaction mixture was cooled to 15°-20° C. poured into previously cooled distilled water (3000 ml) and maintained at 5°-7° C. for 4 hours. The cake was filtered by suction and the formed compound dried at 25°-35° C. under vacuum to obtain a yield of 77.4% (29.2 g) of pivaloyloxymethyl 2-(3'-chloro-2'-methylanilino)-pyridine-3-carboxylate, m.p.: 91° C.-92° C.