Sulfuric Acid → Methyl 2-aminopyridine-3-carboxylate

HRID 1513573Notes

Reaction equation

HRID 1513573 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.[C:16](=O)(O)[O-].[Na+]>CO>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:16])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 729302-Aminonicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 351633Methyl 2-aminopyridine-3-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-aminopyridine-3-carboxylic acid (4.3 g, 31 mmol) in methanol (62 mL) was added dropwise sulfuric acid (31 mL) under ice-cooling, and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was stirred at 70° C. for 15 hr. and neutralized with sodium bicarbonate under ice-cooling. The reaction mixture was extracted twice with ethyl acetate, and the extracts were combined, and washed with brine. The extract was dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (4.3 g, 90%) as a white solid.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at 70° C. for 15 hr
  3. extractionThe reaction mixture was extracted twice with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4403fc9916df4c74ab2c320dbc1a018c
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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