Hydrochloric Acid → HCID 70434271, compound

Participants

Reaction Steps

A mixture of p-nitrobenzaldehyde (1.51 g), β-alanine methyl ester hydrochloride (1.40 g), triethylamine (1.6 ml) and methanol (20 ml) is stirred at room temperature for 25 minutes. The mixture is ice-cooled, and sodium borohydride (807 mg) is added thereto. The mixture is stirred at the same temperature for 10 minutes. The mixture is acidified with 10% HCl, and extracted with ethyl acetate. The aqueous layer is neutralized with 10% NaOH, and extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and then distilled to remove the solvent. The residue is dissolved in ether, and a HCl-ether solution is added thereto. The precipitates are collected and recrystallized from methanol to give N-(p-nitrobenzyl)-β-alanine methyl ester hydrochloride (1.95 g, 71.1%) as pale yellow plates, m.p. 219.5°-220° C. (decomp.).

Provenance & Evidence