Hydrochloric Acid → 4-(2-Aminopyridin-4-yl)benzaldehyde

Participants

Reaction Steps

A stream of HCl gas was bubbled into a suspension of tert-butyl 4-(4-formylphenyl)pyridin-2-ylcarbamate (2-1, 486 mg, 1.63 mmol) in EtOAc (50 mL) at 0° C. for 2 min. The acidified solution was allowed to reach 23° C. and was then stirred for 18 h. The reaction mixture was concentrated to give 4-(2-aminopyridin-4-yl)benzaldehyde (2-2) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 10.07 (s, 1H), 8.18 (d, 1H, J=5.5 Hz), 7.97 (d, 2H, J=8.6 Hz), 7.74 (d, 2H, J=8.1 Hz), 6.91 (dd, 1H, J=5.5, 1.5 Hz), 6.73 (s, 1H), 4.61 (s, 2H).

Provenance & Evidence