Hydrochloric Acid → Ethyl 5-aminopyridine-3-carboxylate

HRID 488453

Reaction equation

HRID 488453 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].Cl.[CH2:12](O)[CH3:13]>>[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH2:12][CH3:13])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3543165-Aminonicotinic Acid

Product 1

HCID 910920Ethyl 5-aminopyridine-3-carboxylate

Procedure

5-Aminonicotinic acid (2.2 g) (Bachman and Micucci, J. Amer. Chem. Soc. 70 (1948) 2381) in ethanol (20 ml) was ice-cooled, saturated with HCl gas and refluxed 4 hours. The mixture was concentrated to low volume and partitioned between EtOAc (100 ml) and saturated NaHCO3 solution (100 ml). The organic phase was washed with further aqueous NaHCO3, dried and evaporated to leave the title compound as a white solid (1.34 g). M.S. (+ve ion chemical ionisation) m/z 167 (MH+,100%).

Workup

  1. temperaturerefluxed 4 hours
  2. concentrationThe mixture was concentrated to low volume
  3. custompartitioned between EtOAc (100 ml) and saturated NaHCO3 solution (100 ml)
  4. washThe organic phase was washed with further aqueous NaHCO3
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-143667ca793a4c3d9c92b1bad47432ed
Source dataset
uspto-grants-2005_12
Patent number
US06972297B2

Linked notes

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