1,1-Dimethylhydrazine → 4-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzonitrile

Participants

Reaction Steps

To a solution of 4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}benzaldehyde (8) (0.920 g, 2.5 mmol) in MeOH (25 mL) was added N,N-dimethylhydrazine (0.341 mL, 4.5 mmol). The resultant mixture was stirred at room temperature for 12 h under N2. Reaction mixture was concentrated under reduced pressure and the residue was re-dissolved in CH3CN (25 mL) to which were added dimethylsulfate (0.378 mL, 3 mmol) and K2CO3 (0.415 g, 3 mmol) under N2. The reaction mixture was refluxed for 24 h. Reaction mixture was cooled at room temperature and poured into water (100 mL). Reaction mixture was extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford the crude product. The product was purified by column chromatography using hexanes:EtOAc (19:1 to 9:1) as an eluent to afford 0.560 g (62%) of the title compound (237) as an off-white solid. IR (film) 2958, 2225, 1602, 1501, 1235 cm−1. 1H NMR (400 MHz, CDCl3): δ 7.66 (d, J=9.2 Hz, 1H), 7.60 (s, 1H), 7.37 (d, J=6.4 Hz, 2H), 7.29-7.23 (m, 3H), 7.15 (d, J=2.4 Hz, 1H), 7.11 (d, J=1.6 Hz, 1H), 7.09 (d, J=1.6 Hz, 1H), 7.08 and 7.05 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.64 (d, J=6.8 Hz, 2H), 3.94 (s, 3H), 2.25 (s, 3H). LCMS (ESI) m/z 366.11 (M+H)+.

Provenance & Evidence