Hydrochloric Acid → HCID 131717722, compound

Participants

Reaction Steps

A solution of 0.97 g of sodium nitrite is 6 ml of water is added dropwise at 0° to 5° C. to a mixture of 3.47 g of 3-(7-amino-2-naphthyl)-5-methoxymethyl-2-oxazolidone, 6 ml of water and 3.3 ml of conc. hydrochloric acid. After the mixture is stirred for a few minutes, 100 ml of methanol are added thereto. The mixture is stirred at room temperature for 7 hours and then allowed to stand in a refrigerator overnight. The reaction mixture is extracted with ethyl acetate and the extract is washed and dried. The aqueous layer is further extracted with chloroform and the extract is dried. The residue (1.88 g) is purified by silica gel column chromatography [solvent: ethyl acetate-hexane (1:1)]. 5-methoxymethyl-3-(7-methoxy-2-naphthyl)-2-oxazolidone [Example 14, m.p. 95.5°-96.5° C. (recrystallized from ethyl acetate-hexane)] and 3-(7-hydroxy-2-naphthyl)-5-methoxymethyl-2-oxazolidone [Example 15 , m.p. 155°-157° C. (recrystallized from ethyl acetate-hexane)] are obtained.

Provenance & Evidence