Acetic Anhydride → HCID 20475370, compound

HRID 2295393Notes

Reaction equation

HRID 2295393 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[N+:4]([O-])[C:3]=1[C:10]1[N+:11]([O-:16])=[CH:12][CH:13]=[CH:14][CH:15]=1.[C:17]([O:20]C(=O)C)(=[O:19])[CH3:18]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([C:10]2[N+:11]([O-:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:4][C:5]([CH2:8][O:20][C:17](=[O:19])[CH3:18])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178425646HCID 178425646, compound

Product 1

HCID 20475370HCID 20475370, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4 g (0.018 mol) of 3,6-dimethyl-2,2'-bipyridine 1,1'-dioxide in 20 ml chloroform is added dropwise, at 60° C. and under a nitrogen atmosphere, to 20 ml of acetic anhydride. The mixture is stirred for 20 hours at 60°-65° C. and then concentrated in vacuo. After the addition of 50 ml of water and 50 ml of ethyl acetate, the mixture is rendered alkaline with potassium carbonate. The water phase is separated off and washed with four times 50 ml of ethyl acetate/THF (ratio about 2:1 by volume). The combined organic phases are dried over sodium sulfate. After the solvent has been distilled off in vacuo, 4.44 g (96% of theory) of a brown crude product are obtained, which can be caused to crystallise at 0° C. The crude product can be employed direct for further reactions. After recrystallisation from diethyl ether, 73% of pure 3-methyl-6-acetoxymethyl-2,2'-bipyridine 1' -oxide are obtained; melting point 105°-107° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionAfter the addition of 50 ml of water and 50 ml of ethyl acetate
  3. customThe water phase is separated off
  4. washwashed with four times 50 ml of ethyl acetate/THF (ratio about 2:1 by volume)
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. distillationAfter the solvent has been distilled off in vacuo, 4.44 g (96% of theory) of a brown crude product
  7. customare obtained
  8. customto crystallise at 0° C
  9. customAfter recrystallisation from diethyl ether, 73% of pure 3-methyl-6-acetoxymethyl-2,2'-bipyridine 1' -oxide
  10. customare obtained

Sources & evidence

ORD record
ord-6cecd27819f649b496ec955807dfc098
Source dataset
uspto-grants-1984_01
Patent number
US04424359

Reaction notes

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