Sodium Hydroxide → HCID 20505467, compound

Participants

Reaction Steps

Methyl 2-azido-4-cyanobutyrate (1.1 g, 6.55 mmol) was dissolved into a solution of sodium hydroxide in 90% ethanol (7 ml of 1N) and the resultant solution let stand at room temperature for 45 min. Thin layer chromatography (silica, 10% ether-benzene) indicated the reaction was completed. The reaction mixture was diluted with water (7 ml) and stirred (5 min) with Dowex 50W-X8 (acidic, H+ form) resin and then filtered. The filtrate was concentrated under reduced pressure to half the volume (to remove EtOH) and the remaining solution extracted with chloroform (5×10 ml). The chloroform solution, after drying, was evaporated to give 0.89 g (89%) of the title acid as a liquid; ir (neat) νmax : 3200, 2250, 2110, 1740 cm-1 ; 1Hmr (CDCl3) δ: 2.23 (m, 2H, CH2), 2.57 (m 2H, CH2CN) and 4.27 ppm (q, J1 =9, J2 =6 Hz, 1H, CHN3). Anal. calcd for C5H6N4O2 : C 39.62, H 3.92, N 36.36; found: C 39.00, H 3.85, N 36.10.

Provenance & Evidence