Hydroxylamine → HCID 68871617, compound

Participants

Reaction Steps

A solution of the product from Step 4 (2.6 g, 6.5 mmol) in methanol (30 mL), water (20 mL) and 6M HCl (8 mL) was treated with NaNO2 (670 mg, 9.75 mmol) portionwise over 10 min then allowed to stir at rt for 1 h. The reaction mixture was poured into water and extracted with EtOAc. The organic phases were combined, washed with brine, dried (MgSO4), filtered and the filtrate concentrated to give a dark solid which was suspended in dioxane (20 mL) and treated with triethylamine (3 mL) and NH2OH (50% aqueous solution, 650 uL) and then heated to 90° C. for 2 h, then cooled to rt. The reaction mixture was poured into aq. NH4Cl and extracted with EtOAc. The organic phases were combined, washed with brine, dried (MgSO4), filtered and the filtrate concentrated to give a brown solid which was resuspended in dioxane (15 mL) and triethylamine (3 mL) and heated to 140° C. in a sealed tube for 3 h, then cooled to rt. The reaction mixture was poured into aq. NH4Cl and extracted with EtOAc. The organic phases were combined, washed with brine, dried (MgSO4), filtered and the filtrate concentrated to give the title compound (1.66 g, 57%) as a tan solid. MS (ES+) m/e 444 [M+H]+.

Provenance & Evidence