Hydrochloric Acid → (4-Methylphenyl)(pyridin-2-yl)methanone

HRID 742327Notes

Reaction equation

HRID 742327 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1.[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)#N.Cl.CC[O:23]CC>O1CCCC1>[CH3:11][C:8]1[CH:9]=[CH:10][C:5]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:23])=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 3283Diethyl Ether2×HCID 7522Pyridine-2-carbonitrileHCID 78054-BromotolueneHCID 5462224Magnesium

Product 1

HCID 3018781(4-Methylphenyl)(pyridin-2-yl)methanoneYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 250 mL flask were placed 1.425 g (58.5 mmol) of magnesium turnings, 35 mL of anhydrous ether and a iodine crystal. Next, 10 g (58.8 mmol) of 4-bromotoluene dissolved in 70 mL of ether was added dropwise. After the addition was complete, the resulting mixture was heated at reflux for 30 min. Then a solution of 6 g (58.5 mmol) of 2-cyanopyridine in 35 mL of anhydrous tetrahydrofuran was added dropwise and the reaction mixture was stirred at room temperature overnight. The resulting mixture was poured into 1N HCl and extracted several times with ethyl acetate. The organic phase was dried and the solvent was removed, to afford a crude product that was chromatographed on silica gel (hexane-ethyl acetate mixtures of increasing polarity) to give 7.2 g of the desired product (yield: 62%).

Workup

  1. customIn a 250 mL flask were placed
  2. additionwas added dropwise
  3. additionAfter the addition
  4. temperaturethe resulting mixture was heated
  5. temperatureat reflux for 30 min
  6. extractionextracted several times with ethyl acetate
  7. customThe organic phase was dried
  8. customthe solvent was removed
  9. customto afford a crude product that
  10. customwas chromatographed on silica gel (hexane-ethyl acetate mixtures of increasing polarity)

Sources & evidence

ORD record
ord-905c37e2c7b5496d805702e798686598
Source dataset
uspto-grants-1996_09
Patent number
US05554624

Reaction notes

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