Hydrochloric Acid → 2,5-Diphenyl-pyrrol-1-ylamine

Participants

Reaction Conditions

Reaction Steps

A suspension of (2,5-Diphenyl-pyrrol-1-yl)-carbamic acid tert-butyl ester (3.7 g, 11.06 mmol) in anhydrous methanol (25 mL) was cooled to 0° C. in an ice water bath, then treated with conc. HCl (9.86 mL). The ice bath was removed, and the resulting suspension was heated to reflux in an oil bath for 1.5 h. Upon cooling to rt, a white solid precipitated, which was filtered, washed with water and dried in vacuo to afford 2,5-Diphenyl-pyrrol-1-ylamine (2.32 g, 90%): 1H NMR (CDCl3, chemical shifts in ppm relative to TMS): 3.64 (bs, 2H), 6.28 (s, 2H), 7.28-7.33 (m, 2H), 7.42 (t, 4H, J=8.0 Hz), 7.58 (d, 4H, J=8.0 Hz).

Provenance & Evidence