N#N.[H-].[Na+].[CH3:5][C:6]1[CH:18]=[CH:17][C:16]2[NH:15][C:14]3[CH:13]=[CH:12][C:11]4[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=4[C:9]=3[C:8]=2[CH:7]=1.S(OCC)(O[CH2:27][CH3:28])(=O)=O.C(O)C(O)C(O)C(O)C(O)C=O.[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.C(Cl)Cl.O>[CH2:27]([N:15]1[C:14]2[CH:13]=[CH:12][C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[C:9]=2[C:8]2[CH:7]=[C:6]([CH3:5])[CH:18]=[CH:17][C:16]1=2)[CH3:28]To a RB flask equipped with magnetic stirring bar, reflux condenser, rubber septum and N2 inlet line was added a 50% oil dispersion of NaH (7.47 g, 0.155 mol). The oil was removed by washing the dispersion with hexane (3×100 mL). Dry THF (100 mL) was added to the flask by cannula to cover the NaH. A solution of 10-methyl-7H-benzo[c]carbazole (Cambridge Chemicals, Inc., 30.0 g, 0.113 mol) in THF (250 mL) was added to the flask by cannula. The mixture was stirred for 30 min at RT. Diethyl sulfate (Aldrich, 24.1 g, 0.156 mol, 20.4 mL) was then added to the flask by syringe and the resulting mixture stirred overnight at RT. H2O (20 mL) was added to the flask to destroy excess NaH. The mixture was then extracted with CH2Cl2 (3×1 L). The organic layers were combined and washed sequentially with H2O (3×500 mL), saturated NaCl solution (3×500 mL), dried (Na2SO4) and concentrated to give a 38.7 g of a crude oil. This material was passed through a plug of Magnesol® using CH2Cl2 as the eluting solvent. The appropriate fractions were combined and the solvent removed to give after drying 34.1 g of a crude oil. This material was recrystallized from CH3OH to give 28.3 g (84.0%) of 7-ethyl-10-methyl-7H-benzo[c]carbazole, mp 69°-70°, (C,H,N).
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