Dichloromethane → HCID 20548496, compound

HRID 2058875Notes

Reaction equation

HRID 2058875 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)=[CH:7][N:6]([CH3:18])[CH:5]=1)(=[O:3])C.ClN1C(=O)CCC1=O.[Cl:27][CH2:28][Cl:29]>>[Cl:27][CH:28]([Cl:29])[C:1]([C:4]1[C:9](=[O:10])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)=[CH:7][N:6]([CH3:18])[CH:5]=1)=[O:3]

Participants

4

Reactant 3

HCID 6344Dichloromethane3×HCID 31398Chlorosuccinimide2×HCID 132018143-Acetyl-5-(3-chlorophenyl)-1-methylpyridin-4(1H)-one

Product 1

HCID 20548496HCID 20548496, compound

Procedure

A 1.1 g. portion of 3-acetyl-5-(3-chlorophenyl)-1-methyl-4(1H)-pyridinone was dissolved in 100 ml. of dichloromethane, and to it was added dropwise a solution of 1.06 g. of N-chlorosuccinimide in 50 ml. of dichloromethane. After the addition, the reaction mixture was stirred at reflux for 2 days, during which time two additional 0.5 g. portions of N-chlorosuccinimide were added. The mixture was then cooled, diluted with additional dichloromethane, and washed twice with 2 N sodium hydroxide solution. The organic portion was dried over magnesium sulfate, filtered and evaporated under vacuum. The residue was recrystallized from dichloromethane/hexane to obtain 0.4 g. of the desired product, m.p. 201°-202°. Nmr analysis in DMSOd6 showed peaks at δ8.50-8.55 (d, 1H, pyridine); 8.10-8.16 (d, 1H, pyridine); 7.3-8.8 (m, 5H, aromatic and CHCl2); 3.81 (s, 3H, N--CH3).

Workup

  1. additionAfter the addition
  2. temperatureat reflux for 2 days, during which time two additional 0.5 g
  3. temperatureThe mixture was then cooled
  4. washwashed twice with 2 N sodium hydroxide solution
  5. dry with materialThe organic portion was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue was recrystallized from dichloromethane/hexane
  9. customto obtain 0.4 g

Sources & evidence

ORD record
ord-99f776a69ac2413bbf3830316509a1a1
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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