反应详情

A suspension of 4-(4-(ethyl(2-hydroxyethyl)amino)phenyl)naphthalene-1,2-dione (8.5 g, 26.48 mmol) in absolute ethanol (150 ml) was treated in one portion with hydroxylamine hydrochloride (3.68 g, 52.96 mmol) recrystallised from 75:25 EtOH:H2O and stirred at RT for 2 hrs. The mixture was then evaporated in vacuo and the residue suspended in H2O (500 ml). The aqueous phase was then basified to pH 10 with ammonium hydroxide solution and extracted into EtOAc (×4). The combined organics were then dried (Na2SO4) and evaporated in vacuo to afford the product, 4-(4-(ethyl(2-hydroxyethyl)amino)phenyl)-2-(hydroxyimino)naphthalen-1(2H)-one, as a dark red solid (9.1 g, 100%). Analysis of the product by 1H NMR gave a spectrum consistent with the structure.

1. customrecrystallised from 75:25 EtOH
2. customThe mixture was then evaporated in vacuo
3. extractionextracted into EtOAc (×4)
4. dry with materialThe combined organics were then dried (Na2SO4)
5. customevaporated in vacuo