Water → HCID 13771602, compound

Participants

Reaction Steps

To a suspension of 4-Hydroxy--(4-hydroxybutyl)-1-(3-methoxyphenyl)(1,8)-naphthyridin-2(1H)-one (1 g.)in methylene chloride (10 ml),in an ice-acetone bath was added a solution of bromine (0.5 g.) in methylene chloride (5 ml.) over a period of 15 min. The resulting yellow-orange suspension was stirred overnight at room temperature. To the resulting clear yellow solution was added a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (1 g.), in methylene chloride (5 ml.) during 5 mins. The mixture was stirred at room temperature for 3 hrs. after which time water (5 ml) was added. The organic layer was separated, dried and evaporated. To the residue was added 50% aqueous ethanol (10 ml.) and after some time the solid was filtered off and recrystallized from isopropanol to yield 1-(3-methoxyphenyl)-3', 4',5', 6'-tetrahydrospiro[1,8-naphthyridine-3,2'-(2 H)pyran]-2, 4-dione, m.p. 181°-183° C.

Provenance & Evidence