Methyl iodide → Diazene, 1-(4-methoxyphenyl)-2-(4-nitrophenyl)-

Participants

Reaction Steps

Aqueous KOH (0.3 M, 6 mL) was added to a solution of 14 (0.21 g, 1 mmol) in CH2Cl2 (50 mL). After stirring for 10 min, the precipitate was filtered, washed with cold H2O (10 mL), and dried. The resulting solid was suspended in CH2Cl2 (50 mL) and MeI (150 μL, 2 mmol) was added (see FIG. 25). The mixture was heated for 40 h under reflux and Ar. After cooling to ambient temperature, the mixture was washed with water (20 mL). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography [SiO2: hexanes/CH2Cl2 (1:1)] resulting in 11 (0.10 g, 52%) as an orange solid. mp=151° C.; FABMS: m/z=258 [M+H]+; 1H-NMR (400 MHz, chloroform-d): δ=3.88 (3H, s), 6.99-7.01 (2H, m), 7.93-7.95 (4H, m), 8.30-8.33 (2H, m); 13C-NMR (100 MHz, CDCl3): δ=55.9, 114.7, 123.3, 124.9, 125.8, 147.2, 148.5, 156.2, 163.5.

Provenance & Evidence