Ethanol → Ethyl 2-aminopyridine-4-carboxylate

HRID 1789793Notes

Reaction equation

HRID 1789793 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][N:13]=1)[C:8]([OH:10])=[O:9])(=O)C.C([O-])(O)=O.[Na+].[CH2:19](O)[CH3:20]>>[CH2:19]([O:10][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][N:13]=[C:5]([NH2:4])[CH:6]=1)[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 37744662-Acetamidopyridine-4-carboxylic acid

Product 1

HCID 7015521Ethyl 2-aminopyridine-4-carboxylateYield 79%

Procedure

2-Acetylamino-isonicotinic acid (10.8 g, 60.0 mmol) was suspended in ethanol (150 mL) and BF3OEt2 (22 mL, 138 mmol) was added. The mixture was refluxed overnight, and after cooling to room temperature 10% NaHCO3 (250 mL) was added. The product was extracted with chloroform and the combined organic extracts were washed with water and dried. Filtering and concentration afforded 2-amino-isonicotinic acid ethyl ester (7.46 g, 79%) as pale yellow crystals.

Workup

  1. additionBF3OEt2 (22 mL, 138 mmol) was added
  2. temperatureThe mixture was refluxed overnight
  3. additionwas added
  4. extractionThe product was extracted with chloroform
  5. washthe combined organic extracts were washed with water
  6. customdried
  7. filtrationFiltering
  8. concentrationconcentration

Sources & evidence

ORD record
ord-cecb5bf832084ef5a6421240cee3dddf
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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