Hydrochloric Acid → Methyl p-nitrophenylalanine hydrochloride

Participants

Reaction Steps

Dry methanol (200 ml) was saturated with HCl(g) in a two-necked round bottom flask cooled to -10° C. p-Nitrophenylalanine (10.0 g, 47.6 mmol) was added in one portion and left to stir for about 18 hours, the solution was evaporated to near dryness on a rotary evaporator and the precipitated product collected in a Buchner funnel. After drying under vacuum at about 50° C., the yield was 10.97 grams (88.3%). A TCL (thin layer chromatography) of the free amino ester run in CHCl3 :MeOH (4:1) revealed an Rf =0.85-0.88. 1H NMR (220 MHz, D2O, pH 1.5) 8.20 (d, 2 J=10.0), 7.53 (d, 2, J=10.0), 4.55 (t, 1, J=5.00), 3.84 (s, 3), 3.43 (m, 2); CI-MS 225 ((M+1)/z).Anal. Calcd. for C10H13N2O4Cl: C, 46.07; H, 5.03; N, 10.74; Cl, 13.60. Found: C, 45.87; H, 5.08; N, 10.48; Cl, 13.58.

Provenance & Evidence