Methyl iodide → Methyl 2-aminopyridine-3-carboxylate

HRID 1774287Notes

Reaction equation

HRID 1774287 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-].[K+].[K+].IC>CN(C)C=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 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 729302-Aminonicotinic acid

Product 1

HCID 351633Methyl 2-aminopyridine-3-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-aminonicotinic acid (833 mg, 6.00 mmol) and potassium carbonate (912 mg, 6.60 mmol) in dimethylformamide (DMF, 8.5 ml) was heated to reflux. The reaction mixture was cooled to room temperature and 415 μl of iodomethane (6.60 mmol) were added. The mixture was then refluxed under stirring for 18 h; after subsequent cooling, the mixture was finally filtered and the filtrate was concentrated under reduced pressure. The crude product was purified is by flash chromatography on silica gel (ethyl acetate/petroleum ether=7/3). The isolated 2-aminonicotinic acid methyl ester was obtained in 58% yield.

Workup

  1. temperaturewas heated to reflux
  2. temperatureThe mixture was then refluxed
  3. filtrationafter subsequent cooling, the mixture was finally filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-a2c926c777f94f63a4c3f95226b898fd
Source dataset
uspto-grants-2016_02
Patent number
US09260394B2

Reaction notes

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