Ethanol → Ethyl 2-(3-chloropyridin-2-yl)propanoate

HRID 2197601Notes

Reaction equation

HRID 2197601 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]([CH3:11])[C:9]#N)=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.C(=O)(O)[O-:18].[Na+].[CH2:22]([OH:24])[CH3:23]>>[Cl:1][C:2]1[C:3]([CH:8]([CH3:11])[C:9]([O:24][CH2:22][CH3:23])=[O:18])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 674989082-(3-Chloropyridin-2-yl)propanenitrile

Product 1

HCID 67500197Ethyl 2-(3-chloropyridin-2-yl)propanoateYield 91%

Conditions

Temperature
0 °C

Procedure

The product of Example 38A (1.15 g, 6.9 mmol) was dissolved in absolute ethanol (14 mL) and cooled to 0° C. Concentrated sulfuric acid (13.54 g, 7.36 mL, 138 mmol) was added, and the reaction mixture was allowed to warm to ambient temperature. The reaction was then heated at reflux for 2 hours, cooled, and poured onto ice. The mixture was neutralized with saturated aqueous sodium bicarbonate, and extracted with two portions of ethyl acetate. The organic layers were separated and concentrated to give the title compound (1.34 g, 91%) which was used without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.49 (dd, J=1.5, 4.7, 1H), 7.93 (dd, J=1.5, 8.1, 1H), 7.36 (dd, J=4.7, 8.1, 1H), 4.29 (q, J=7.1, 1H), 4.07 (q, J=7.1, 2H), 1.42 (d, J=7.1, 3H), 1.11 (t, J=7.1, 3H). MS (DCI) m/z 214 (M+H)+.

Workup

  1. temperatureto warm to ambient temperature
  2. temperatureThe reaction was then heated
  3. temperatureat reflux for 2 hours
  4. temperaturecooled
  5. additionpoured onto ice
  6. extractionextracted with two portions of ethyl acetate
  7. customThe organic layers were separated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-14261e06602b443a8f8343e792a49f06
Source dataset
uspto-grants-2012_12
Patent number
US08338603B2

Reaction notes

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