Hydrochloric Acid → 1-(4-Methylpyridin-3-yl)propan-1-one

HRID 1830895Notes

Reaction equation

HRID 1830895 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#N)=[CH:6][N:5]=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-:12].[Na+].[CH2:16](OCC)[CH3:17]>>[CH3:1][C:2]1[CH:3]=[CH:4][N:5]=[CH:6][C:7]=1[C:8](=[O:12])[CH2:16][CH3:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 2278064-Methyl-3-cyanopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 131426831-(4-Methylpyridin-3-yl)propan-1-one

Procedure

A solution of 4-methylnicotinonitrile (5.90 g) in diethyl ether (75 ml) was cooled to 5° C. and an ethylmagnesium bromide diethyl ether solution (3.0M, 25 ml) was gradually added thereto. The reaction mixture was heated under reflux for 2 hrs. and added to 1N hydrochloric acid (200 ml). The mixture was stirred at room temperature for 30 min. Sodium bicarbonate was added to neutralize the reaction mixture, and the mixture was 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=3:1–2:1) for purification to give the title compound (5.07 g) as a pale-red oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. extractionthe mixture was extracted 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=3:1–2:1) for purification

Sources & evidence

ORD record
ord-ad6eca31c14d4cb49730d10d7bbc658f
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

Loading…