Sodium Cyanide → Ethyl 5-(cyanomethyl)-2-pyridinecarboxylate

HRID 1526072Notes

Reaction equation

HRID 1526072 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12]Cl)=[CH:8][N:7]=1)=[O:5])[CH3:2].[C-:14]#[N:15].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:14]#[N:15])=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 21698088Ethyl 5-(chloromethyl)pyridine-2-carboxylate

Product 1

HCID 50853204Ethyl 5-(cyanomethyl)-2-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.5 g (52.6 mmol) 5-(chloromethyl)pyridine-2-carboxylic acid ethyl ester [preparation according to H. Barth et al., Liebigs Ann. Chem. 1981, 2164-2179] are initially introduced into 75 ml anhydrous DMF and 2.58 g (52.6 mmol) sodium cyanide are added in portions at RT in the course of 3 h. The mixture is then introduced on to 500 ml saturated ammonium chloride solution and extracted with methylene chloride (four times with 100 ml each time). The combined organic phases are dried over sodium sulfate and concentrated and the residue is purified by chromatography over silica gel (mobile phase: cyclohexane→cyclohexane/ethyl acetate 1:4). 3.80 g (38% of th.) of the title compound are obtained.

Workup

  1. additionare added in portions at RT in the course of 3 h
  2. extractionextracted with methylene chloride (four times with 100 ml each time)
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is purified by chromatography over silica gel (mobile phase: cyclohexane→cyclohexane/ethyl acetate 1:4)

Sources & evidence

ORD record
ord-9f47f858767e4f98bf79cedcd9f452f5
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

Loading…