[CH2:1]1[N:6]([C:7]2[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4]OC1.Cl.[CH3:16][NH:17][OH:18].[C:19](=[O:22])([O-])[O-].[Na+].[Na+]>O.C(O)C>[OH:18][N:17]([CH3:16])[C:13](=[NH:14])[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]1[CH2:1][CH2:19][O:22][CH2:4][CH2:5]1To a stirred solution of 2-(4-morpholino)benzonitrile (3.76 g, 20 mmol) and N-methylhydroxylamine hydrochloride (3.34 g, 40.0 mmol) in 1:1 water/ethanol (100 mL) was added sodium carbonate (2.12 g, 20 mmol) and the resulting mixture stirred at 90° C. overnight. After cooling and concentrating, the resulting residue was suspended in MeOH/CHCl3 (1:9). The insoluble solids were removed by filtration and concentration of the mother liquor gave the title product as an amber oil (3.8 g) that was carried on without further purification. LCMS calcd for C12H18N3O2 (M+H): 236.13; found: 236.31.
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