Isopropanol → HCID 24692243, compound

HRID 1983580Notes

Reaction equation

HRID 1983580 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][N:9]=1>O>[CH:1]([O:4][C:8]1[CH:13]=[C:12]([CH:11]=[CH:10][N:9]=1)[C:14]#[N:15])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 24692243HCID 24692243, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To isopropanol (30.0 mL) was added sodium hydride (0.606 g of 60% dispersion, 15.2 mmol) in small portions over 5 minutes. The resulting gel-like suspension was stirred for an additional 5 minutes at room temperature. 2-Chloro-4-cyanopyridine (2.00 g, 14.4 mmol) was then added in one portion and the resulting solution was heated to reflux. After 1 hour, the reaction mixture was allowed to cool to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried (magnesium sulfate) and concentrated to provide a yellow oil. Flash chromatography over silica (hexanes/ethyl acetate) afforded 1.25 g (53%) of product as a colorless oil: 1H NMR (CDCl3) δ 8.27 (d, J=5.2 Hz, 1H), 7.01 (dd, J=5.2, 1.4 Hz, 1H), 6.91 (d, J=1.4 Hz, 1H), 5.31 (sept, J=6.2 Hz, 1H), 3.33 (d, J=6.2 Hz, 6H) ppm.

Workup

  1. temperaturethe resulting solution was heated to reflux
  2. waitAfter 1 hour
  3. temperatureto cool to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customto provide a yellow oil

Sources & evidence

ORD record
ord-013e7a62fbd84fac9cc88f715229102f
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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