Sodium Hydroxide → 6-Bromo-4-chlorocinnoline

Participants

Reaction Conditions

Reaction Steps

A solution of Example 34C (0.4 g, 1.8 mmol) in POCl3 (2.5 mL) was heated to 100° C. for 2 hours, and poured slowly onto ice. The aqueous layer was cooled to 0° C. and adjusted to pH 5-7 with 50% NaOH. The aqueous layer was extracted with ethyl acetate (2×50 mL), and the combined organic layers were concentrated. The residue was purified by flash column chromatography on silica gel with 4:1 hexanes/ethyl acetate to provide the desired product (0.190 g, 43%).

Provenance & Evidence