Anthranilic Acid → 2-Phenylquinoline-8-carboxylic acid

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A mixture of conc. H2SO4 (45 mL), water (5 mL), AcOH (5 mL), anthranilic acid (XI; R2 =H) (20.5 g) and H3AsO4 (80% w/w; 32 g) was heated with stirring to 105° C., and then treated with cinnamaldehyde (VIII; R1 =H) (25 g) at the rate which maintained the temperature at 105°-110° C. The reaction mixture was stirred for a further 3 h at 110°-115° C., then cooled and strongly basified with aqueous KOH. The aqueous layer was decanted from a quantity of tar, washed with CHCl3 and then acidified with AcOH. The resulting precipitate was chromatographed on SiO2 and eluted with a gradient of MeOH in CH2Cl2 to give a low yield of the desired acid, mp 160°-161° C., identical in all respects to the compound obtained in Example A. This compound was elaborated to compound 1 of Table I by the method outlined in Example A.

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