Dimethyl Sulfate → 6-Acetylaminomethyl-2-pyridinecarbonitrile

HRID 2379819Notes

Reaction equation

HRID 2379819 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[O-])(=[O:3])[CH3:2].S(OC)(OC)(=O)=O.[C-:20]#[N:21].[K+]>CS(C)=O>[C:1]([NH:4][CH2:5][C:6]1[N:7]=[C:8]([C:20]#[N:21])[CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 9032Potassium Cyanide2×HCID 301083N-[(1-oxidopyridin-1-ium-2-yl)methyl]acetamide

Product 1

HCID 99897406-Acetylaminomethyl-2-pyridinecarbonitrileYield 15.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-acetylaminomethylpyridine N-oxide (1.00 g) and dimethyl sulfate (0.63 ml) was stirred for three hours. Dimethyl sulfoxide (6 ml) and potassium cyanide (392 mg) were added to the mixture and the solution was stirred for two hours at ambient temperature. Additional potassium cyanide (392 mg) was added to the mixture and which was further stirred for two hours. After the solvent was removed by concentration, the residue was mixed with water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (15 g) by eluting with a mixture of ethyl acetate and methanol (20:1) to give 6-acetylaminomethyl-2-pyridinecarbonitrile (0.16 g).

Workup

  1. stirringthe solution was stirred for two hours at ambient temperature
  2. stirringwas further stirred for two hours
  3. customAfter the solvent was removed by concentration
  4. additionthe residue was mixed with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel (15 g)
  9. washby eluting with a mixture of ethyl acetate and methanol (20:1)

Sources & evidence

ORD record
ord-c90a05a56a2847178cc417415fb809e5
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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