Methanol → Methyl 2-aminopyridine-3-carboxylate

HRID 215687Notes

Reaction equation

HRID 215687 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[CH3:15]O>>[CH3:15][O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][CH:13]=[N:14][C:6]=1[NH2:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 729302-Aminonicotinic acid

Product 1

HCID 351633Methyl 2-aminopyridine-3-carboxylateYield 55%

Procedure

42.4 g (356.4 mmol, 26 ml) thionyl chloride was added dropwise to a suspension of 15.0 g (108.6 mmol) 2-aminonicotinic acid in 150 ml abs. Methanol, while cooling. The mixture was heated to reflux and the mixture was refluxed for 19 hours. The evolving SO2 was scrubbed. The solvent was removed under reduced pressure after cooling down to room temperature. The residue was carefully treated with a satured NaHCO3 solution and extracted with ethyl acetate. The organic fraction was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. 9.13 g (55%) of 2-aminonicotinic acid methyl ester was isolated as a pale yellow solid (m.p. 83° C.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturethe mixture was refluxed for 19 hours
  4. customThe solvent was removed under reduced pressure
  5. additionThe residue was carefully treated with a satured NaHCO3 solution
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic fraction was dried over magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-44311b2c45b94b29b982197b92097dfa
Source dataset
uspto-grants-2012_06
Patent number
US08192918B2

Reaction notes

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