2-Aminonicotinic acid → Methyl 2-aminopyridine-3-carboxylate

HRID 2079937Notes

Reaction equation

HRID 2079937 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:11](=O)(O)[O-].[Na+]>CO.S(=O)(=O)(O)O>[CH3:11][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 729302-Aminonicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 351633Methyl 2-aminopyridine-3-carboxylateYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

2-Amino-nicotinic acid (10.0 g, 72.4 mmol) was dissolved in a mixed solution of methanol (200 mL) and sulfuric acid (10 mL), and the solution was stirred under reflux for 35 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution at 0° C., which was extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography to obtain the title compound (5.26 g, 34.6 mmol, 48%) as a white solid.

Workup

  1. temperatureunder reflux for 35 hours
  2. extractionwhich was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-473685286def4c418382feca65ce2279
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…