C[O-].[Na+].[ClH:4].[NH2:5][OH:6].Cl[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[C:13]2[CH2:18][C:19]#[N:20]>CO>[OH:6][N:5]=[C:19]([NH2:20])[CH2:18][C:13]1[C:14]2[C:9](=[C:8]([Cl:4])[CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1A mixture of NaOMe (25 wt % in MeOH, 1.02 mL, 4.46 mmol), MeOH (4 mL), and hydroxylamine hydrochloride (310 mg, 4.46 mmol) was heated at reflux for 20 minutes. 5-Chloro-2-naphthalenylacetonitrile (600 mg, 2.98 mmol) and additional MeOH (4 mL) were added and heating was continued overnight. Additional hydroxylamine hydrochloride (150 mg, 2.16 mmol) and NaOMe (25 wt % in MeOH, 490 μL, 2.14 mmol) were added and heating was resumed for 4 hours. The mixture was cooled, concentrated, and suspended in H2O. The solid was collected by filtration and triturated with ether to give a pale yellow solid (478 mg, 69%), m.p. 121°-125° C.
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