Water → Methyl [3-chloro-6-(methyloxy)-[1,5]naphthyridin-4-yl]acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of dimethyl[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanedioate (56.23 g, 173 mmol) in DMSO (1210 ml) was added lithium chloride (14.9 g, 350 mmol) and water (3.24 ml, 180 mmol). The mixture was heated to 100° C. for 16 h then cooled and treated with ethyl acetate and water. The organic phase was washed twice with water, the aqueous extracted with ethyl acetate and this water-washed. The combined organic phases were dried and the solvent was removed. The residue was subjected to column chromatography on silica gel using a hexane and ethyl acetate gradient to provide the desired compound containing a little of the starting material (43.3 g, 94%).

Provenance & Evidence