Water → 2-Acetyl-6-(acetylaminomethyl)pyridine

HRID 2379795Notes

Reaction equation

HRID 2379795 reaction equation
[CH3:1][Mg]Br.[C:4]([NH:7][CH2:8][C:9]1[N:14]=[C:13]([C:15]#N)[CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH3:5].[OH2:17]>O1CCCC1>[C:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:8][NH:7][C:4](=[O:6])[CH3:5])[N:14]=1)(=[O:17])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 99897406-Acetylaminomethyl-2-pyridinecarbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 103753152-Acetyl-6-(acetylaminomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An ethereal solution of methyl magnesium bromide (3 mol/l) (17.6 ml) was added dropwise to a solution of 6-(acetylaminomethyl)-2-pyridinecarbonitrile (3.70 g) in tetrahydrofuran (60 ml) at 5° to 10° C. with stirring. After the mixture was stirred for two hours at the same temperature, cold water (15 ml) was dropped to the mixture under ice-cooling and evaporated in vacuo. The residue was mixed with water and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography by eluting with a mixture of ethyl acetate and methanol (50:1) to give 2-acetyl-6-(acetylaminomethyl)pyridine (2.70 g).

Workup

  1. additionwas dropped to the mixture under ice-
  2. temperaturecooling
  3. customevaporated in vacuo
  4. additionThe residue was mixed with water
  5. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  6. dry with materialThe extract was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washby eluting with a mixture of ethyl acetate and methanol (50:1)

Sources & evidence

ORD record
ord-0fb53d8c31e545b19d4e8c23a91495e5
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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