Water → HCID 86744736, compound

Participants

Reaction Steps

15.6 g of N-acetyl-N'-methylcyclopropylethylenediamine are refluxed during two hours with 80 ml of 15% hydrochloric acid. The solution is then saturated with sodium hydroxide, extracted with ethyl ether, the organic extract is dried and evaporated at 20° C./15 mm/Hg. Gas-chromatographically pure N-acetyl-N'-methyl-N'-cyclopropylethylene is thus obtained. 8.06 g (0.04 mole) of 2-methoxy-4-amino-5-chlorobenzoic acid and 7.12 g (0.044 mole) of carbonyldiimidazole are suspended in 80 ml of tetrahydrofuran and kept at 30° C. until the gas evolution stopped. A solution containing 5.7 g (0.05 mole) of N-methyl-N-cyclopropylethylenediamine in 15 ml of tetrahydrofuran is then slowly added at room temperature, and thereafter the temperature is kept at 50° C. for one hour. After cooling down, the mixture is poured into water, the solid is removed by filtration and crystallized from alcohol, thus obtaining 9.6 (80.6%) of 2-methoxy-4-amino-5-chloro-N-(2-(methylcyclopropylamino)ethyl-benzamide having a melting point of 164°-5° C. Hydrochloride, m.p. 130°-2° C.

Provenance & Evidence