[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:4]=1[NH2:5].COC1C=CC=[C:17]([NH2:21])C=1N.[H][H].N#CBr>[Pd].CO.C(#N)C.O>[CH3:1][O:2][C:3]1[C:4]2[N:5]=[C:17]([NH2:21])[NH:10][C:6]=2[CH:7]=[CH:8][CH:9]=1The material was prepared by the catalytic reduction of 2-methoxy-6-nitroaniline to 3-methoxybenzene-1,2-diamine using a hydrogen atmosphere at 40 psi and 10% palladium on carbon (50% w/w water) in methanol. The resulting crude diamine was subsequently reacted with cyanogen bromide in an acetonitrile-water mixture according to previous procedure and used without further purification. 1H-NMR (400 MHz, CDCl3), δ 12.40 (bs, 1H), 7.26 (d, 1H), 7.15 (t, 1H), 6.77 (d, 1H), 6.59 (bs, 2H), 3.73 (s, 3H). MS (EI): 164 (MH+).
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