Bromine → 4-Chloroquinolin-2-amine

Participants

Reaction Steps

Bromine (2.32 mL) was dissolved in 5% aqueous potassium hydroxide solution (190 mL), and a solution of 4-chloroquinoline-2-carboxamide [product of Example 262 (1), 9.80 g] in tetrahydrofuran (190 mL) was dropwise added thereto. The mixture was stirred at room temperature for 30 min, and the mixture was stirred at 80° C. for 1 hr with heating. The reaction mixture was filtrated and the filtrate was added to water. The mixture was extracted with chloroform, and the extract was washed with brine-and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 2-amino-4-chloroquinoline (1.98 g) as a pale-yellow solid.

Provenance & Evidence