Ethanol → Diethyl 2,4-pyridinedicarboxylate

HRID 714451Notes

Reaction equation

HRID 714451 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][C:2]=1[C:10]([OH:12])=[O:11].O.[C:14]1(C)C=CC(S(O)(=O)=O)=C[CH:15]=1.[CH2:25](O)[CH3:26]>C1(C)C=CC=CC=1>[CH2:14]([O:11][C:10]([C:2]1[CH:3]=[C:4]([C:7]([O:9][CH2:25][CH3:26])=[O:8])[CH:5]=[CH:6][N:1]=1)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 103652,4-Pyridinedicarboxylic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 170509Diethyl 2,4-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4.7 g (28.12 mmol) of 2,4-pyridinedicarboxylic acid and 8.02 g (42.19 mmol) of 4-toluenesulfonic acid monohydrate were suspended in 47 ml of toluene, the mixture was heated to 110° C. and 170 ml (2.87 mol) of ethanol were slowly added dropwise. The reaction mixture was stirred under reflux overnight. The reaction mixture was evaporated and the residue was purified by column chromatography on silica gel 60 (mobile phase: dichloromethane/ethanol 40/1→10/1).

Workup

  1. temperatureunder reflux overnight
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by column chromatography on silica gel 60 (mobile phase: dichloromethane/ethanol 40/1→10/1)

Sources & evidence

ORD record
ord-239b310539404e70a19caaa058e09211
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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