Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][NH2:11].CO[CH:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17].C[O-].[Na+]>C(O)C>[NH2:19][C:18]1[N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH3:2])[N:11]=[CH:14][C:15]=1[C:16]#[N:17]To a solution of 1-(2-methoxyphenyl)hydrazine hydrogen chloride (3 g, 0.017 mol) in ethanol (50 mL) was added 2-(methoxymethylene)malononitrile (1.89 g, 0.9 eq.) and sodium methoxide (1.92 g, 2.1 eq). The reaction mixture was heated at reflux for 18 h and concentrated. The reaction mixture was partitioned between brine and ethyl acetate. The organic layer was separated, dried with magnesium sulfate, filtered and concentrated. MPLC Biotage chromatography eluting with 20-60% ethyl acetate/hexanes afforded the title compound in 53% yield (1.9 g). 400 MHz 1H NMR (CDCl3) δ 7.64 (m, 1 H), 7.40 (m, 2H), 7.08 (m,2H), 4.51 (bs, 2H), 3.87 (s, 3 H); MS: (M+H m/z=215.2).
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