Trifluoroacetic acid → HCID 89545313, compound

Participants

Reaction Steps

To a suspension of 2-amino-5-bromopyridine (2.34 g, 13.5 mmol) and p-formaldehyde (3.0 g) in toluene (50 mL) was added trifluoroacetic acid (0.1 mL) and the reaction mixture was heated at reflux for 16 h, allowed to cool to ambient temperature, filtered through a pad of diatomaceous earth and concentrated in vacuo. The residue was triturated in methanol to afford 5-bromo-N-methylenepyridin-2-amine as a colorless solid in 34% yield (0.849 g): 1H NMR (300 MHz, CDCl3) δ8.13 (s, 1H), 7.48 (dd, J=8.9, 2.4 Hz, 1H), 6.86 (d, J=8.9 Hz, 1H), 5.51 (s, 2H); MS (ES+) m/z 184.9 (M+1), 186.9 (M+1).

Provenance & Evidence