Ethyl formate → 2-(2-Chloropyridin-3-yl)-3-oxopropanenitrile

HRID 911112Notes

Reaction equation

HRID 911112 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]#[N:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH:13](OCC)=[O:14]>C1COCC1>[Cl:1][C:2]1[C:7]([CH:8]([CH:13]=[O:14])[C:9]#[N:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 147395432-(2-Chloropyridin-3-yl)acetonitrile

Product 1

HCID 866141612-(2-Chloropyridin-3-yl)-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-chloropyridin-3-yl)acetonitrile (2.0 g, 13 mmol) in THF (5 mL) was slowly added to a suspension of sodium hydride, 60% in mineral oil (1.31 g, 33.0 mmol) in THF (10 mL) at 0° C. The mixture was stirred for 15 minutes, and ethyl formate (1.1 mL, 13 mmol) was slowly added. The mixture was stirred at RT, and monitored by LCMS. Upon completion, the reaction was extracted into EtOAc, washed organics 2×H2O, dried with Mg2SO4, filtered through fritted funnel, and lyophilized to yield 2-(2-chloropyridin-3-yl)-3-oxopropanenitrile as reddish brown solid. The crude was used without further purification. MS m/z=181 [M+1]+. Calc'd for C8H5ClN2O: 180.59.

Workup

  1. stirringThe mixture was stirred at RT
  2. extractionUpon completion, the reaction was extracted into EtOAc
  3. washwashed organics 2×H2O
  4. dry with materialdried with Mg2SO4
  5. filtrationfiltered through fritted funnel

Sources & evidence

ORD record
ord-fa18f96b12944545ba76dc9b968366be
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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