Sodium Carbonate → 2-Chloro-6-methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 6-methoxyquinoline N-oxide (5.0 g, 29 mmol) in CHCl3 (30 mL) was treated by slow addition of POCl3 (5.3 mL, 57 mmol) at 0° C. The mixture was heated at 80° C. for 14 hours. The mixture was cooled and poured onto ice. After stirring for 30 min., the aqueous layer was adjusted to pH 9 by Na2CO3 addition. The mixture was extracted with CH2Cl2. The organic layer was worked-up. HPLC (1:10 EtOAc/hexane) gave 2.5 g (46%) of 2-chloro-6-methoxyquinoline as a white solid, (M+) 193(100).

Provenance & Evidence