Acetic Acid → HCID 22348064, compound

Participants

Reaction Steps

4-Chloroaniline (2.55 g, 20 mmol) and 4-pyridinecarboxaldehyde (1.9 mL, 20 mmol) were dissolved in dichloroethane (80 mL) prior to addition of glacial acetic acid (5 mL). The solution was stirred for 15 minutes before portionwise addition of sodium triacetoxyborohydride (4.23 g, 20 mmol). Analysis by TLC showed the reaction was complete after stirring at room temperature for 3 hours. The reaction was diluted with ethyl acetate, washed several times with 1N NaOH, and dried with sodium sulfate. Evaporation at reduced pressure gave the title amine (3.61 g). 1H NMR (300 MHz, CDCl3) δ ppm 4.27 (2H, d, J=5.89), 6.42 (2H, m), 7.02 (2H, m), 7.19 (2H, m), 8.45 (2H, m).

Provenance & Evidence