Methanol → Methyl 2-aminopyridine-3-carboxylate

HRID 1361972Notes

Reaction equation

HRID 1361972 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) □ 8.22 (dd, 1H), 8.13 (dd, 1H), 6.63 (dd, 1H), 6.30 (br s, 2H), 3.89 (s, 3H).

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-8b96d831e7ed419fafa82fc942c945a5
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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