Sulfuric Acid → HCID 23371895, compound

Participants

Reaction Steps

200 mg (0.7 mmol) of (RS)-3-(3-amino-4-cyclohexyl-phenyl)-5-methoxymethyl-oxazolidin-2-one were suspended in a mixture of 0.86 ml of water, 0.72 g of ice and 0.235 ml of conc. sulfuric acid and treated at 0°-50 with a solution of 45 mg (0.66 mmol) of sodium nitrite in 0.4 ml of water. After boiling under reflux for 3 hours the mixture was extracted with dichloromethane, dried with sodium sulfate and the solvent was distilled off. Chromatography over silica gel with ethyl acetate/hexane 1:2 gave 120 mg (60%) of white crystals with m.p. 207°-208°.

Provenance & Evidence