Hydrochloric Acid → 4-(AMINOMETHYL)-3-METHOXYBENZONITRILE

Participants

Reaction Steps

10.6 ml of hydrazine hydrate were added to 21.2 g (73 mmol) of 4-phthalimidomethyl-3-methoxybenzonitrile dissolved in 290 ml of THF, and the mixture was stirred at room temperature for 20 h. Then 180 ml of 2H [sic] HCl were added dropwise and, after 1.5 h, the solvent was completely stripped off. The residue was taken up in MTBE, extracted with 1N HCl, adjusted to pH 9-10 with 2N NaOH and extracted with methylene chloride. 8.0 g (68%) of product were obtained. 1H-NMR (DMSO-d6 ; δ in ppm): 7.55 (dd, 1H); 7.40 (dd, 1H; 7.37 (d, 1); 3.85 (s, 3H); 3.70 (s, 2H); 2.5-1.6 (NH2).

Provenance & Evidence