Water → HCID 86753175, compound

HRID 2395257Notes

Reaction equation

HRID 2395257 reaction equation
[C:1]([C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](CCl)=[CH:15][N:14]=1.O>CN(C)C=O.C(#N)C>[Cl:12][C:13]1[C:18]([N:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[C:4]2=[O:9])=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 5775433-Cyano-2-pyridone

Product 1

HCID 86753175HCID 86753175, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

2.0 g (0.017 mol) of 3-cyano-2-pyridone (Brana, Rodriguez, J. Heterocycl. Chem., 1297 (1982)) are dissolved in 30 ml of absolute N,N-dimethylformamide, and 0.56 g (0.019 mol) of sodium hydride (80% suspension) are added at 0° C. After the mixture has been stirred for 20 minutes, a solution of 2.75 g (0.017 mol) of 2-chloro-5-chloromethyl pyridine in 10 ml of absolute acetonitrile is added dropwise, and the mixture is stirred for 3 hours at room temperature. The reaction mixture is then poured into 400 ml of water and extracted using ethyl acetate, and the organic phase is dried over magnesium sulphate and then distilled to dryness. The residue is stirred with a little diethyl ether and filtered off with suction. In this manner, 3.2 g of 1-(2'-chloropyridin-3-yl)-3-cyano-2-pyridone of melting point 145° C. are obtained.

Workup

  1. stirringthe mixture is stirred for 3 hours at room temperature
  2. extractionextracted
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. distillationdistilled to dryness
  5. stirringThe residue is stirred with a little diethyl ether
  6. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-78243c0a975f43edad72971ece77e1df
Source dataset
uspto-grants-1998_09
Patent number
US05814645

Reaction notes

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