Methyl iodide → Methyl 2-amino-6-chloronicotinate

HRID 1774289Notes

Reaction equation

HRID 1774289 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:12][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[N:10][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 122639922-Amino-6-chloronicotinic acid

Product 1

HCID 57415887Methyl 2-amino-6-chloronicotinateYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-amino-6-chloronicotinic acid (500 mg, 2.90 mmol) and is potassium carbonate (441 mg, 3.19 mmol) in DMF (5 ml) was heated to reflux. The reaction mixture was cooled to room temperature and 273 μl of iodomethane (4.35 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 by flash chromatography on silica gel (ethyl acetate/petroleum ether=95/5). The isolated 2-amino-6-chloronicotinic acid methyl ester was obtained in 54% 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 by flash chromatography on silica gel (ethyl acetate/petroleum ether=95/5)

Sources & evidence

ORD record
ord-a83bcf4cdf5d4c66afdc27cb18bc1f4c
Source dataset
uspto-grants-2016_02
Patent number
US09260394B2

Reaction notes

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