4-Chlorophenol → 6-Chloro-9-(4-chlorophenoxy)-2-methoxyacridine

Participants

Reaction Conditions

Reaction Steps

A reaction mixture consisting of 1.39 g (5.0 mmol) of 6,9-dichloro-2-methoxyacridine and 3.0 g (23 mmol) of p-chlorophenol was heated at 80° C. for 4 h. The hot reaction mixture was poured into hot 5% aqueous NaOH. The combined solution was stirred until a fine yellow crystalline precipitate appeared. The crystals were filtered, washed to neutrality with water and dried at 70° C. in vacuo. Recrystallization from pyridine afforded 6-chloro-9-(p-chlorophenoxy)-2-methoxyacridine as yellow microcrystals, yield 1.06 g (57%), mp 151.5°-153° C.; λ max (CH3OH) 400, 381, 351, 333, 318 (sh) and 262 nm; 1H-NMR (CDCl3, (CH3)4Si) δ 3.76 (s, 3) 6.7-6.9 (m, 2) 7.1-7.6 (m, 5) and 7.8-8.2 (m, 3).

Provenance & Evidence