Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.[O-]S([O-])(=O)=O.[Na+].[Na+].Cl.[CH3:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:20]([CH3:32])=[CH:19][C:18]=1[NH2:33].Cl.[NH2:35][OH:36].C([O-])(O)=O.[Na+]>O>[CH3:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:20]([CH3:32])=[CH:19][C:18]=1[NH:33][C:3](=[O:5])[CH:2]=[N:35][OH:36]To a solution of chloral hydrate (910 mg, 5.5 mmol) in 12 mL of water were added, in order: 13 g of anhydrous Na2SO4; a solution of 2,5-dimethyl-4-(2-morpholin-4-yl-ethoxy)-pheylamine hydrogen chloride (1.61 g, 5 mmol) in water (3 mL); and finally, a solution of hydroxylamine hydrochloride (1.12 g, 16 mmol) in 5 mL of water. The mixture was heated in an oil bath (130° C.) with stirring for 15 min, then cooled down to room temperature, diluted with water, neutralized to pH 7 with concentrate aq. NaHCO3, and extracted with EtOAc. The combined organic layer was was washed with water, dried (Na2SO4) and concentrated under reduced pressure to give N-[2,5-dimethyl-4-(2-morpholin-4-yl-ethoxy)-phenyl]-2-hydroxyimino-acetamide as yellow solid (1.45 g, 91%).
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