Hydrochloric Acid → HCID 23371865, compound

Participants

Reaction Steps

180 mg (0.6 mmol) of (RS)-3-(3-amino-4-cyclohexyl-phenyl)-5-methoxymethyl-oxazolidin-2-one (from the mother liquor of the foregoing reaction) were suspended in a mixture of 0.32 ml of water, 0.32 g of 37 percent hydrochloric acid and 0.64 g of ice and treated with a solution of 41.4 mg (0.6 mmol) of sodium nitrite in 0.3 ml of water at 0°-5°. After stirring at this temperature for 30 minutes a solution of 0.1 g (0.6 mmol) of potassium iodide in 0.3 ml of water was added. The mixture was stirred at room temperature overnight, extracted with ethyl acetate and chromatographed over silica gel with ethyl acetate/hexane 3:1 to give 100 mg of oil. MS: m/e (% basic peak): 415 (M+, 100), 372 (5), 346 (9), 289 (9), 245 (12), 143 (15), 71 (22).

Provenance & Evidence