Dimethylformamide → 2,4-Dimethoxyquinoline

Participants

Reaction Steps

2,4-Dichloroquinoline (cf. example 14) (4.4 g), sodium methoxide (5.4 g) and dimethyl formamide (70 ml) were heated together at 70° for 2 hrs. The reaction mixture was partitioned between water and ethyl acetate and worked up in standard fashion. The crude product was purified by column chromatography on silica (10% ether in hexane) to give 2-methoxy-4-chloroquinoline (0.87 g) and 2,4-dimethoxyquinoline (1.8 g). The latter was subjected to aqueous hydrolysis by 6N hydrochloric acid for 3 hrs at reflux temperature to give 2-hydroxy-4-methoxyquinoline. This was converted to 2-chloro-4-methoxyquinoline.

Provenance & Evidence