2-CHLOROQUINOLINE-4-CARBOXYLIC ACID

Uses

Synthesis

15733-89-8

5467-57-2

The general procedure for the synthesis of 2-chloroquinoline-4-carboxylic acid from 2-quinolone-4-carboxylic acid was as follows: 2-hydroxyquinoline-4-carboxylic acid (2.57 g, 13.6 mmol) was mixed with phosphorus oxytriphosphate (POCl3, 25 mL) and heated and refluxed for 24 hours. Upon completion of the reaction, the reaction mixture was quenched by slowly pouring it into crushed ice (300 g). The precipitated solid was separated by filtration, washed thoroughly with deionized water and dried under high vacuum to give 2.47 g of white solid product in 87% yield. The product was characterized by 1H NMR (CDCl3, 300 MHz) and LCMS: 1H NMR δ 8.67 (d, 1H, J = 8.4 Hz), 7.91 (d, 1H, J = 8.1 Hz), 7.83 (s, 1H), 7.67 (t, 1H, J = 7.2 Hz), 7.54 (t, 1H, J = 7.2 Hz); LCMS (m/ z): 208 ([M+H]+).

References