Methanol → Methyl 2-aminopyridine-3-carboxylate

HRID 1825969Notes

Reaction equation

HRID 1825969 reaction equation
OS(O)(=O)=O.[NH2:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:16]O>>[NH2:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:16])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 729302-Aminonicotinic acid

Product 1

HCID 351633Methyl 2-aminopyridine-3-carboxylateYield 71%

Procedure

Concentrated H2SO4 (20 mL, 360 mmole) was added dropwise over 5 minutes to a suspension of 2-aminonicotinic acid (25 g, 181 mmole) in MeOH (400 mL), and the mixture was heated at reflux; a homogeneous solution formed within 5 min. After 72 h, the reaction was cooled to room temperature and concentrated under vacuum. The residue was basified with 1.0 N Na2CO3 (500 mL) (Gas evolution!) and extracted with EtOAc (500 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated to dryness to give the title compound (19.6 g, 71%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.22 (dd, 1 H), 8.13 (dd, 1 H), 6.63 (dd, 1 H), 6.30 (br s, 2 H), 3.89 (s, 3 H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customa homogeneous solution formed within 5 min
  4. concentrationconcentrated under vacuum
  5. extractionextracted with EtOAc (500 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-51f2e39cf4b4403db8171142c3296836
Source dataset
uspto-grants-2006_05
Patent number
US07049310B2

Reaction notes

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