Ethanol → 4-{[2-(4-Hydroxyphenyl)ethyl]-[1,2,4]triazol-4-yl-amino}benzonitrile

Participants

Reaction Steps

To a stirred solution of 4-{[2-(4-benzyloxyphenyl)ethyl]-[1,2,4]triazol-4-yl-amino}benzonitrile (536 mg, 1.355 mmol) in distilled THF (15 mL) was added in succession absolute ethanol (30 mL) and Pd/C (10%, 54 mg). The black suspension was then stirred under an atmosphere of hydrogen (balloon) for 3 days. Upon removal by filtration and washings of the supported catalyst exhaustively with distilled THF, the filtrate was evaporated to give a pale yellow syrup which solidified upon standing at room temperature to a light yellow wax (192 mg). This crude was fractionated by flash chromatography (ethyl acetate) and the second fraction that separated gave 4-{[2-(4-hydroxyphenyl)ethyl]-[1,2,4]triazol-4-yl-amino}benzonitrile as a pale yellow waxy residue (115 mg, 376.6 μmol, 28%); Rf 0.46 (neat ethyl acetate), c.f. 0.59 (S.M.); δH (400 MHz, DMSO-d6) 2.70 (2H, t, J 7.4 Hz, CH2CH2N), 4.01 (2H, t, J˜7.6 Hz, CH2N), 6.59 (2H, AA′BB′), 6.69 (2H, AA′BB′), 7.06 (2H, AA′BB′), 7.71 (2H, AA′BB′), 8.78 (2H, s, C3′-H and C5′-H) and 9.29 (1H, s, exchanged with D2O, OH); LRMS (FAB+): 611.2[12, (2M+H)+], 459.1[8, (M+H+NBA)+], 306.0[100, (M+H)+]; (FAB−): 763.5[18, (2M+NBA)−], 609.4[45, (2M−H)−], 184.0[100, (HOPhCH2CH2)−]; HRMS (FAB+) 306.13477 C17H16N5O requires 306.13549.

Provenance & Evidence