Propionitrile → 2-methyl-3-oxo-3-(pyridin-3-yl)propanenitrile

HRID 530023Notes

Reaction equation

HRID 530023 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[H-].[Na+].[C:14](#[N:17])[CH2:15][CH3:16]>C1(C)C=CC=CC=1>[CH3:16][CH:15]([C:1](=[O:9])[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[C:14]#[N:17]

Participants

5

Reactant 3

HCID 7854PropionitrileHCID 24758Sodium hydrideHCID 69188Ethyl Nicotinate

Product 1

HCID 431572262-methyl-3-oxo-3-(pyridin-3-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Under a N2 atmosphere ethyl nicotinate (3 g, 0.02 mol) and NaH (1.6 g, 0.04 mol) were suspended in toluene (30 mL) and heated to 90° C. Propiononitrile (2.2 g, 0.04 mol) was added dropwise and the reaction was stirred at 90° C. overnight. After cooling to room temperature, the solid was filtered and collected. The solid was dissolved in water (50 mL) and washed with ethyl acetate (30 mL). The aqueous layer was adjusted to pH=6 with 2M HCl and extracted again with ethyl acetate (30 mL×2). The combined ethyl acetate extracts were combined and dried over Na2SO4, filtered and concentrated in vacuo to give the desired product: 1HNMR (400 MHz, CDCl3) δ 9.25 (d, 1 H, J=1.2 Hz), 8.90 (d, 1 H, J=4.8 Hz), 8.33 (d, 1 H, J=8.0 Hz), 7.54 (dd, 1 H, J=1.2 Hz, J=8.0 Hz), 4.37-4.39 (m, 1 H), 1.71 (d, 3 H, J=7.2 Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was filtered
  3. customcollected
  4. dissolutionThe solid was dissolved in water (50 mL)
  5. washwashed with ethyl acetate (30 mL)
  6. extractionextracted again with ethyl acetate (30 mL×2)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46f848d4fde94aed8b9231b4dcb0252f
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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