Formic Acid → N-(2-Cyanoethyl)-N-formylglycine

HRID 1607907Notes

Reaction equation

HRID 1607907 reaction equation
C([O:3][C:4](=[O:11])[CH2:5][NH:6][CH2:7][CH2:8][C:9]#[N:10])C.[CH:12](O)=[O:13].[OH-].[K+].O>C(O)C>[C:9]([CH2:8][CH2:7][N:6]([CH:12]=[O:13])[CH2:5][C:4]([OH:3])=[O:11])#[N:10]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 521172N-(2-Cyanoethyl)glycine ethyl ester

Product 1

HCID 19849818N-(2-Cyanoethyl)-N-formylglycine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 21.0 g of N-(2-cyanoethyl)-glycine ethyl ester and 18.3 g of formic acid is refluxed for 2 h. After concentration of this mixture underreduced pressure, the residue is taken up in 50 ml of ethanol, and cooled to 0° C.; there is then added dropwise a solution of 25.5 g of potassium hydroxide and 40 ml of water in 80 ml of ethanol. After the reaction solution has warmed up to room temperature, the solvent is evaporated off, and the residue is acidified to pH 1 with conc. hydrochloric acid. The mixture is saturated with sodium chloride and subsequently extracted with ethyl acetate. The combined organic extracts are concentrated by evaporation to thus obtain N-(2-cyanoethyl)-N-formylglycine, m.p. 112°-114° C. (compound No. 1.1).

Workup

  1. temperatureis refluxed for 2 h
  2. temperatureAfter the reaction solution has warmed up to room temperature
  3. customthe solvent is evaporated off
  4. extractionsubsequently extracted with ethyl acetate
  5. concentrationThe combined organic extracts are concentrated by evaporation to thus obtain N-(2-cyanoethyl)-N-formylglycine, m.p. 112°-114° C. (compound No

Sources & evidence

ORD record
ord-3218ba32a7d74467a8304dfb5d1b1349
Source dataset
uspto-grants-1989_09
Patent number
US04868202

Reaction notes

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