Ethanol → HCID 178490399, compound

Participants

Reaction Conditions

Reaction Steps

Using the general procedure of Shine et al., J. Heterocyclic Chem. (1989) 26:125-128, hydroxylamine hydrochloride (22 ml, 5 M, 110 mmol) and sodium hydroxide (11 ml, 10 M, 110 mmol) were added to a solution of 3-methoxybenzonitrile (11.5 ml. 94 mmol) in ethanol (130 ml). The reaction mixture was then heated at reflux (80° C.) for 12 h. After the mixture was cooled, most of the solvent was removed in vacuo. The crude product was partitioned between ethyl acetate and water, washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was removed in vacuo. Flash chromatography on silica gel using 35-50% ethyl acetate in hexane yielded the title compound (8.05 g, 52%). Examples 7-9 were prepared in an analogous method to the procedure given in Example 6.

Provenance & Evidence