Sodium Hydroxide → HCID 20505467, compound

HRID 355249Notes

Reaction equation

HRID 355249 reaction equation
[N:1]([CH:4]([CH2:9][CH2:10][C:11]#[N:12])[C:5]([O:7]C)=[O:6])=[N+:2]=[N-:3].[OH-].[Na+]>C(O)C.O>[N:1]([CH:4]([CH2:9][CH2:10][C:11]#[N:12])[C:5]([OH:7])=[O:6])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20505471HCID 20505471, compound

Product 1

HCID 20505467HCID 20505467, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-2510af9a5fff4062bb0271274b7661b8
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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