反应详情

Hydroxylamine hydrochloride (3.16 g, 0.045 mol) was added to a stirred solution of sodium ethoxide in ethanol [prepared by dissolving 1.17 g of sodium in 70 ml of ethanol]. The mixture was stirred at room temperature for 15 min then 1-cyano-3-tert-butyloxycarbonylaminobenzene (3.00 g, 0.014 mol) was added. The mixture was heated at 50° C. overnight then cooled to ambient temperature. The mixture was then filtered and the filtrate evaporated in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The organic phase was separated and the aqueous phase extracted with ethyl acetate (3×20 ml). The organic layers were combined, washed with brine (50 ml) then dried (Na2SO4). The solvent was evaporated to leave a pink fo.m. The foam was left at 0° C. overnight, then triturated with 1:1 petrol:ethyl acetate. The title compound was collected as a white solid (2.52 g, 73%). 1H NMR (360 MHz, D6 -DMSO)δ1.47 (9H, s), 5.69 (2H, brs), 7.24 (2H, m), 7.41 (1H, brd, J=6.5 Hz), 7.82 (1H, s), 9.35 (1H, s), 9.58 (1H, s). MS (CI, NH3) 252 (M+1).

1. temperatureThe mixture was heated at 50° C. overnight
2. temperaturethen cooled to ambient temperature
3. filtrationThe mixture was then filtered
4. customthe filtrate evaporated in vacuo
5. customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
6. customThe organic phase was separated
7. extractionthe aqueous phase extracted with ethyl acetate (3×20 ml)
8. washwashed with brine (50 ml)
9. dry with materialthen dried (Na2SO4)
10. customThe solvent was evaporated
11. customto leave a pink fo.m
12. waitThe foam was left at 0° C. overnight
13. customtriturated with 1:1 petrol
14. customThe title compound was collected as a white solid (2.52 g, 73%)