7-Fluoro-2-methylisatoicanhydride → Methyl 4-fluoro-2-(methylamino)benzoate

Participants

Reaction Steps

A mixture of 7-fluoro-1-methyl-1H-3,1-benzoxazine-2,4-dione (20.0 g) and methanol (103 ml) was boiled under reflux. To the boiling mixture was added dropwise a solution of sodium methoxide (0.06 g) in methanol (50 ml.) during 19 minutes. The mixture was distilled in vacuo to remove solvent and give the product as a residue. There was thus obtained the novel compound methyl 4-fluoro-2-methylaminobenzoate as an oil which solidified on standing and was suitable for use in the next stage of synthesis. An analytical sample was prepared by distillation in vacuo followed by recrystallisation of the distillate from aqueous isopropanol. This sample had m.p. 39°-39.5°.

Provenance & Evidence