Hydrochloric Acid → Ethyl 5-aminopyridine-2-carboxylate

HRID 2120071Notes

Reaction equation

HRID 2120071 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][CH:7]=1.Cl.[CH2:12](O)[CH3:13]>>[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([O:10][CH2:12][CH3:13])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 41797265-Aminopyridine-2-carboxylic acid

Product 1

HCID 13816714Ethyl 5-aminopyridine-2-carboxylate

Conditions

Temperature
23 °C

Procedure

A stirred suspension of 3-amino-pyridine-6-carboxylic acid (25 g) in ethanol (300 mL) at 0° C. was saturated with gaseous hydrogen chloride. The mixture was allowed to warm to 23° C. and heated to reflux for 2 hours. A clear solution was obtained. After cooling to 23° C., the mixture was concentrated in vacuo, neutralized with aqueous NaHCO3 and extracted with ethyl acetate. The organic phase was washed with water, dried over MgSO4, and concentrated in vacuo to give ethyl 3-amino-pyridine-6-carboxylate as a pale yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customA clear solution was obtained
  4. temperatureAfter cooling to 23° C.
  5. concentrationthe mixture was concentrated in vacuo
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d07cdb8725146c799a144402ccdec56
Source dataset
uspto-grants-2004_02
Patent number
US06689754B1

Reaction notes

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