Sodium hydride → 4,7-bis(4-(N,N-diphenylamino)phenyl)-2-(2-methylquinolin-4-yl)-2H-benzo[d][1,2,3]triazole

Participants

Reaction Conditions

Reaction Steps

A mixture of Intermediate D (605 mg, 1.0 mmol), 4-chloroquinaldine (266 mg, 1.5 mmol), 60% NaH (60 mg, 1.5 mmol), and dimethylformamide (15 mL) was stirred under argon and heated at 160° C. for 4 days. The volatiles were removed under reduced pressure, and the residue was chromatographed using silica gel and hexane/ethyl acetate (2:1) as an eluent. The obtained product was recrystallized from ethanol to give 4,7-bis(4-(N,N-diphenylamino)phenyl)-2-(2-methylquinolin-4-yl)-2H-benzo[d][1,2,3]triazole (Example 15) as orange crystals, 520 mg (70%). 1H NMR (400 MHz, CDCl3): δ 8.73 (d, J=8.4 Hz, 1H, quinaldine), 8.13 (d, J=8.4 Hz, 1H, quinaldine), 8.07 (d, J=8.8 Hz, 4H, p-phenylene), 7.98 (s, 1H, quinaldine), 7.77 (ddd, J=8.4, 7.0 and 1.1 Hz, 1H, quinaldine), 7.73 (s, 2H, benzotriazole), 7.60 (ddd, J=8.4, 7.3 and 1.1 Hz, 1H, quinaldine), 7.25-7.30 (m, 8H, Ph), 7.21 (d, J=8.4 Hz, 4H, p-phenylene), 7.16-7.19 (m, 8H, Ph), 7.05 (tt, J=7.3 and 1.1 Hz, 4H, Ph), 2.86 (s, 3H, quinaldine). UV-vis spectrum (dichloromethane): λmax=438 nm. Fluorimetry (dichloromethane): λmax=617 nm.

Provenance & Evidence