Acetic Acid → HCID 13079860, compound

HRID 2418651Notes

Reaction equation

HRID 2418651 reaction equation
OO.C(O)(=[O:5])C.Cl[C:8]1[C:13]([C:14]2[CH:19]=[CH:18]C=[CH:16][CH:15]=2)=[CH:12][N:11]=[C:10]([CH3:20])[C:9]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].[C:26]([Cl:30])(Cl)(Cl)Cl>>[Cl:30][C:26]1[CH:18]=[CH:19][C:14]([C:13]2[CH:8]=[C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([CH3:20])=[N+:11]([O-:5])[CH:12]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 5943Carbon TetrachlorideHCID 86739657HCID 86739657, compound

Product 1

HCID 13079860HCID 13079860, compound

Procedure

Hydrogen peroxide (100 vol.; 65.6 ml) was added to glacial acetic acid (250 ml) with stirring and the solution was heated to 50°. 5-(p-Chlorophenyl-2-methyl-3-ethoxycarbonylpyridine (27.55 g) was added and the solution stirred at 50°-55° for 16 hours. The volume of the solution was halved by evaporation in vacuo at below 50° C., and the mixture was then poured into water and neutralised with 2M-sodium hydroxide. The precipitate so formed was filtered off and washed with water to give a white solid which was recrystallied from carbon tetrachloride to give, as white crystals, the title compound, m.p. 130°.

Workup

  1. temperaturethe solution was heated to 50°
  2. stirringthe solution stirred at 50°-55° for 16 hours
  3. customThe volume of the solution was halved by evaporation in vacuo at below 50° C.
  4. additionthe mixture was then poured into water and neutralised with 2M-sodium hydroxide
  5. customThe precipitate so formed
  6. filtrationwas filtered off
  7. washwashed with water
  8. customto give a white solid which
  9. customto give, as white crystals

Sources & evidence

ORD record
ord-4615f527b6c1467588941b814b8e92de
Source dataset
uspto-grants-1984_09
Patent number
US04473395

Reaction notes

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