8-chloro-11-(2-(4-methoxyphenyl)hydrazineyl)-5-methyl-5H-indolo[2,3-b]quinoline (**B9**)

Yield, 70%; brownish red solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 8.77 (s, 1H), 8.59 (d, *J* = 8.8 Hz, 1H), 8.21 (d, *J* = 8.8 Hz, 1H), 8.16 (d, *J* = 8.9 Hz, 1H), 8.04 (t, *J* = 8.0 Hz, 1H), 7.68 (t, *J* = 7.7 Hz, 1H), 7.56 (s, 1H), 7.31 (d, *J* = 8.7 Hz, 0H), 7.26–7.17 (m, 1H), 6.93–6.80 (m, 4H), 4.42 (s, 1H), 4.22 (s, 3H), 3.68 (s, 3H). 13C NMR (100 MHz, DMSO) *δ* 154.59, 151.36, 148.39, 147.17, 141.69, 139.42, 138.20, 136.66, 133.47, 130.83, 127.22, 124.56, 122.82, 120.59, 116.85, 115.21(2C), 114.96(2C), 113.84, 111.08, 54.29, 34.56. MS-ESI *m*/*z*: calcd for C23H19ClN4O[M + H]+: 403.1247; found: 403.2404.
