Chlorine → 3-Chloro-1-methyl-5-(pyrazin-2-yl)pyridin-2(1H)-one

HRID 1981513Notes

Reaction equation

HRID 1981513 reaction equation
[Cl:1]Cl.[CH3:3][N:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)[CH:7]=[CH:6][C:5]1=[O:16]>C(O)(=O)C>[Cl:1][C:6]1[C:5](=[O:16])[N:4]([CH3:3])[CH:9]=[C:8]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 136450981-Methyl-5-(pyrazin-2-yl)pyridin-2(1H)-one

Product 1

HCID 136451003-Chloro-1-methyl-5-(pyrazin-2-yl)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

About 1.2 ml of condensed chlorine gas is introduced into a reaction mixture comprising 1-methyl-5-(2-pyrazinyl)-2-pyridone (3.2 g) dissolved in 200 ml of glacial acetic acid. After all the chlorine is added, stirring is stopped and the solid product filtered, washed with ether and air dried. The dried solid is suspended in distilled H2O to which saturated potassium carbonate is added until the pH is greater than 7. The resulting white solid is filtered, recrystallized from isopropanol, and NMR and IR indicate that it is the desired 3-chloro-1-methyl-5-(2-pyrazinyl)-2-pyridone compound, M.P. 197°-198° C.

Workup

  1. filtrationthe solid product filtered
  2. washwashed with ether and air
  3. customdried
  4. additionis added until the pH is greater than 7
  5. filtrationThe resulting white solid is filtered
  6. customrecrystallized from isopropanol, and NMR and IR

Sources & evidence

ORD record
ord-92c4ffb15a5b48918b98ee41222f868a
Source dataset
uspto-grants-1986_06
Patent number
US04593028

Reaction notes

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