Hydroxylamine → HCID 136377090, compound

Participants

Reaction Conditions

Reaction Steps

A solution of hydroxylamine hydrochloride (979 mg, 14.1 mmol) in methanol (15 ml) and a solution of potassium hydroxide (790 mg, 14.1 mmol) in methanol (15 ml) were combined at 0° C. Solid (KCl) was removed by filtration. The filtrate was added to 2-(2′-methylbiphenyl-2-yl)acetonitrile (1.46 g, 7.04 mmol) and heated at 60° C. overnight. An extra equivalent of NH2OH in MeOH solution was added and heating was continued for 5 h. The mixture was cooled and then concentrated in vacuo. The residue was taken up into CHCl3 (30 ml) and to this was added dimethyl acetylenedicarboxylate (1.00 g, 7.04 mmol). The mixture was heated at 60° C. overnight, cooled and evaporated. The residue was transferred to a microwave vial and xylene (8 ml) was added. The vial was capped and heated in the microwave oven at 140° C. for 3 h, cooled. Chromatography (silica gel; 10% to 100% EtOAc in hexanes) provided the desired product as an off-white solid (0.003 g; 0.12%). LCMS: m/z=351 (MH+).

Provenance & Evidence