[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH2:8][CH2:7][C:6]2=O)[CH3:2].N1C=CC=CC=1.Cl.[NH2:22][OH:23].O>C(O)C.ClCCl>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH2:8][CH2:7]/[C:6]/2=[N:22]\[OH:23])[CH3:2]To a solution of 6-ethyl-1-methyl-2,3-dihydroquinolin-4(1H)-one (0.32 g) in ethanol (25 mL) were added pyridine (0.53 g) and hydroxylamine hydrochloride (0.59 g). The mixture was heated to 90° C. for two hours with a reflux condenser attached. The mixture was cooled to room temperature, and the solvent was stripped under reduced pressure. The residue was portioned between water and dichloromethane and the organics were extracted three times. The combined organics were washed once with brine, dried with sodium sulfate, filtered, and concentrated. 0.34 g of the title product were recovered. (98% yield). MS (ESI+) for C12H16N2O m/z 205.02 (M+H)+.
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