4-Methylmorpholine → Methyl 4-[methoxy(methyl)carbamoyl]benzoate

Participants

Reaction Steps

To a solution of Terephthalic acid monomethyl ester (5.4 g, 30 mmol) and 2-chloro-4,6-dimethoxy-[1,3,5]triazine (7.9 g, 45 mmol) in THF (300 mL) is added N-methyl morpholine (4.95 mL, 45 mmol), the mixture is stirred at room temperature overnight. Additional N-methyl morpholine (4.95 mL, 45 mmol) is added, followed by the addition of O, N-dimethyl-hydroxylamine HCl salt (3.51 g, 45 mmol). The reaction mixture is stirred overnight, and filtered through celite. The filtrate was concentrated and purified by column chromatography on silica gel (hexane/ethyl acetate) giving the title compound (6.8 g).

Provenance & Evidence