N,N-Dimethylaniline → 5-acetyl-2-chloro-6-methylnicotinonitrile

HRID 2073860Notes

Reaction equation

HRID 2073860 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=O)[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:25].[OH-].[Na+]>ClC1C=CC=CC=1>[C:1]([C:4]1[C:9]([CH3:10])=[N:8][C:7]([Cl:25])=[C:6]([C:12]#[N:13])[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 27654765-Acetyl-2-hydroxy-6-methylnicotinonitrile

Product 1

HCID 14753755-acetyl-2-chloro-6-methylnicotinonitrile

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

35 g (0.2 mol) of 5-acetyl-3-cyano-6-methyl-2-pyridone* are suspended in 400 ml of chlorobenzene, 24.2 g (0.2 mol) of N,N-dimethylaniline are added, and 37 g (0.24 mol) of POCl3 are added dropwise. The mixture is then heated at 100° C. for three hours. After cooling, the mixture is cautiously poured onto water, neutralization with dilute sodium hydroxide solution is carried out, the organic phase is separated off, and the aqueous phase is again extracted with CHCl3. The combined extracts are dried with Na2SO4 and evaporated. The residue is purified by filtration through silica gel, using CH2Cl2 /ethyl acetate as eluent.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is again extracted with CHCl3
  4. dry with materialThe combined extracts are dried with Na2SO4
  5. customevaporated
  6. filtrationThe residue is purified by filtration through silica gel

Sources & evidence

ORD record
ord-1f1ae1255a154d7f9481a6b8c7848d7a
Source dataset
uspto-grants-1990_04
Patent number
US04920136

Reaction notes

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