Ethanol → Ethyl 5-methylpicolinate

HRID 481292

Reaction equation

HRID 481292 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#N)=[N:11][CH:12]=1.C(=O)([O-])[OH:16].[Na+].[CH2:20]([OH:22])[CH3:21]>>[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([O:22][CH2:20][CH3:21])=[O:16])=[N:11][CH:12]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric Acid2×HCID 741835-MethylpicolinonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 12243769Ethyl 5-methylpicolinate

Procedure

200 ml of ethanol and 100 ml (1.88 mol) of concentrated sulfuric acid were added to 55.5 g of 5-methylpyridine-2-carbonitrile to form a homogeneous solution, followed by heating under reflux for 2 days. The reaction liquid was gradually poured into a saturated aqueous solution of sodium hydrogencarbonate under cooling with ice to neutralize the sulfuric acid, followed by extraction with dichloromethane. The organic layer was washed with a saturated aqueous solution of common salt and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in a reduced pressure to give 78.1 g of a brown oil of the title compound as the crude product.

Workup

  1. customto form a homogeneous solution
  2. temperatureby heating
  3. temperatureunder reflux for 2 days
  4. customThe reaction liquid
  5. temperatureunder cooling with ice
  6. extractionfollowed by extraction with dichloromethane
  7. washThe organic layer was washed with a saturated aqueous solution of common salt
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. concentrationthe filtrate was concentrated in a reduced pressure

Sources & evidence

ORD record
ord-e4e75ecb96984b0594131e7871530136
Source dataset
uspto-grants-1998_08
Patent number
US05789403

Linked notes

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