Sodium Hydroxide → HCID 20505467, compound

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, H30 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.

1. customat room temperature
2. customfor 45 min
3. concentrationfiltered.The filtrate was concentrated under reduced pressure to half
4. customthe volume (to remove EtOH)
5. extractionthe remaining solution extracted with chloroform (5×10 ml)
6. dry with materialThe chloroform solution, after drying
7. customwas evaporated

ORD record

ord-f6078a64058349c5a13e7ea01ad48a53

Source dataset

uspto-grants-1981_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04272437