[C:1]([C:3]1[CH:19]=[CH:18][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH2:20][OH:21]>C(O)C.[Cl-].[Na+].O>[OH:21][N:20]=[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH:13]2[O:14][CH2:15][CH2:16][O:17]2)=[O:8])=[CH:18][CH:19]=1)[NH2:2]To a solution of 3-(1,3-dioxolan-2-yl)propyl 4-cyanobenzoate (1.00 g, 4.38 mmol) in ethanol (5 mL), was added hydroxylamine (50% aqueous solution, 5 mL), and the mixture heated at 80° C. for 4 hours. The reaction was diluted with saturated brine and extracted with ethyl acetate (×3). The combined organic fractions were dried with magnesium sulphate, and the solvent evaporated at reduced pressure. The material was used directly in the next step without further purification.
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