Pyridine → 4-Chlorobenzaldehyde O-(2-cyano-3-pyridylcarbonyl)oxime

HRID 2106722Notes

Reaction equation

HRID 2106722 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:9]1[N:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([O-:13])=[O:12])#[N:8].[K+].[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([CH:24]=[N:25]O)=[CH:22][CH:21]=1.N1C=CC=CC=1>ClCCl>[C:7]([C:9]1[C:10]([C:11]([O:13][N:25]=[CH:24][C:23]2[CH:27]=[CH:28][C:20]([Cl:19])=[CH:21][CH:22]=2)=[O:12])=[CH:14][CH:15]=[CH:16][N:17]=1)#[N:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 2191584-Chloro-benzaldehyde oximeHCID 23690323Potassium 2-cyanonicotinate

Product 1

HCID 544125484-Chlorobenzaldehyde O-(2-cyano-3-pyridylcarbonyl)oximeYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

Oxalyl chloride (2.8 g, 0.022 mole) is added dropwise to a suspension of potassium 2-cyanonicotinate (4.1 g, 0.022 mole) in dichloromethane (40 ml). The mixture is then heated under reflux for one hour. A solution of 4-chlorobenzaldehyde oxime (3.1 g, 0.02 mole) and pyridine (1.6 g, 0.02 mole) in dichloromethane (20 ml) is then added to the mixture, at 20° C. The mixture is then stirred for 2 hours at 20° C. The solvent is evaporated off and the residue treated with water (50 ml). The solid formed is filtered off and is washed with water and then with ethyl ether. A white solid 4.4 g, 77%) corresponding to the structure 2 is thus obtained (M.p.: 160° C.).

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for one hour
  3. customThe solvent is evaporated off
  4. additionthe residue treated with water (50 ml)
  5. customThe solid formed
  6. filtrationis filtered off
  7. washis washed with water

Sources & evidence

ORD record
ord-76b59c7518a94de0ae8fdc482899f3e1
Source dataset
uspto-grants-1990_06
Patent number
US04931456

Reaction notes

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