Hydrochloric Acid → 1-Butanone, 3-methyl-1-(4-methyl-3-pyridinyl)-

HRID 1830897Notes

Reaction equation

HRID 1830897 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#N)=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:10]([Mg]Br)[CH:11]([CH3:13])[CH3:12].Cl.C([O:19]CC)C>>[CH3:10][CH:11]([CH3:13])[CH2:12][C:8]([C:7]1[CH:6]=[N:5][CH:4]=[CH:3][C:2]=1[CH3:1])=[O:19]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 2278064-Methyl-3-cyanopyridineHCID 178418816HCID 178418816, compound

Product 1

HCID 220498061-Butanone, 3-methyl-1-(4-methyl-3-pyridinyl)-

Procedure

A solution of 4-methylnicotinonitrile (5.00 g) in diethyl ether (75 ml) was cooled to 5C and a solution (ca. 0.8 M, 78 ml) of isobutylmagnesium bromide in diethyl ether was gradually added thereto. The mixture was heated under reflux for 24 hrs. and added to 1N hydrochloric acid (400 ml). The mixture was stirred at room temperature for 2 hrs. The reaction mixture was neutralized, and extracted with ethyl acetate. The organic layer was dried and concentrated, and the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=3:1) for purification to give the title compound (3.20 g) as a pale-yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hrs
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=3:1) for purification

Sources & evidence

ORD record
ord-99ca8474e293466aaf116a7310cea047
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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