Aniline → N-Phenylglycine ethyl ester

Participants

Reaction Steps

To a 250 mL round-bottom flask equipped with addition funnel and argon inlet was added 50 mL of aniline III which was stirred mechanically at 0° C. under argon atmosphere Ethyl bromoacetate, 25 mL (224 mmol) was added in dropwise fashion over 60 min. The mixture slowly solidified and was allowed to stand unstirred at -25° C. for 18 hours. The solid was chipped from the flask and partitioned between dichloromethane (CH2Cl2) and water. The aqueous layer was made basic with 20 mL 50 NaOH solution and extracted with CH2Cl2. The combined organic layers were washed well with H2O, dried over MgSO4 and concentrated. The residue was crystallized from hexane containing a trace of CH2Cl2. Total yield was 28 g (156 mmol, 70% yield) based on ethyl bromoacetate used. mp. 54°-55° C., 'H-NMR (CDCl3) ppm δ7.19 (t, 2 H, J= 7 Hz), 6.76 (t,1 H, J=7 Hz), 6.60 (d, 1 H, J=7 Hz), 4.24 (q, 2 H, J=7 Hz), 3.89 (S,2 H), 1.29 (t, 3 H, J=7 Hz; IR (KBr) 3420, 1742, 1610, 1520, 1220 cm-1.

Provenance & Evidence