Toluene → 2-Methyl-1-(pyridin-3-yl)propan-1-one

HRID 1613644Notes

Reaction equation

HRID 1613644 reaction equation
O1CCN(C([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)C#N)CC1.[OH-:16].[Na+].[CH:18](Br)([CH3:20])[CH3:19].[C:22]1(C)C=CC=CC=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:18]([C:20]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:16])([CH3:22])[CH3:19]

Participants

7

Reactant 4

HCID 1140TolueneHCID 63582-BromopropaneHCID 14798Sodium HydroxideHCID 303572(Morpholin-4-yl)(pyridin-3-yl)acetonitrile

Product 1

HCID 122813372-Methyl-1-(pyridin-3-yl)propan-1-one

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

133 g (0.70 mol) of alpha-morpholino-3-pyridylacetonitrile, 25.7 g (0.07 mol) of tetrabutylammonium iodide, 278 g (3.5 mol) of 50% strength NaOH, 250 ml (2.65 mol) of isopropyl bromide and 300 ml of toluene, as a two-phase system, were heated at 50° C. for 4 hours with thorough mixing. Working up was carried out by adding water, separating the phases and washing the organic phase three times with water. After the solvent had been distilled off, the crude product in the form of an oil was added dropwise to half-concentrated H2SO4 at 60° C. After 2 hours, the mixture was brought to pH 9 with 50% strength NaOH and was extracted with toluene. The organic phase was washed three times with water and the wash solution was extracted 4 times with toluene. The collected toluene extracts were dried over Na2SO4 and filtered and the filtrate was evaporated down. The product was obtained as a dark oil.

Workup

  1. customseparating the phases
  2. washwashing the organic phase three times with water
  3. distillationAfter the solvent had been distilled off
  4. additionthe crude product in the form of an oil was added dropwise to half-concentrated H2SO4 at 60° C
  5. extractionwas extracted with toluene
  6. washThe organic phase was washed three times with water
  7. extractionthe wash solution was extracted 4 times with toluene
  8. dry with materialThe collected toluene extracts were dried over Na2SO4
  9. filtrationfiltered
  10. customthe filtrate was evaporated down
  11. customThe product was obtained as a dark oil

Sources & evidence

ORD record
ord-8daa1337d82542628b20ed2a6baf94a4
Source dataset
uspto-grants-1993_03
Patent number
US05194441

Reaction notes

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