Nitrogen → HCID 19865441, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(1,2-dihydro-4-hydroxy-1-phenyl-2-oxo-1,8-naphthyridin-3-yl)-pyrrolidinium hydroxide, inner salt (3 g), triethylamine (1.88 g), and diethylcarbamoyl chloride (1.57 g) in dry pyridine (50 mL) was stirred overnight at room temperature in an N2 atmosphere. Some starting material remained so dimethylformamide (50 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (2.83 g), and diethylcarbamoyl chloride (1.57 g) were added and the mixture was heated at 80° C. for 0.5 hour. The reaction mixture was then poured over ice and the pH was adjusted to about 6 with acetic acid. The resulting solution was extracted three times with ethyl acetate. The organic extracts were combined, dried (Na2SO4), filtered and evaporated to a solid which was recrystallized from isopropanol to yield the desired product, 2.03 g (54%), m.p. 158°-160° C.

Provenance & Evidence