Methyl iodide → Methyl 2-chloronicotinate

HRID 1814785Notes

Reaction equation

HRID 1814785 reaction equation
[Cl: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-].[Cs+].[Cs+].IC.C(OCC)(=O)C>CN(C=O)C>[CH3:11][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[N:10][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 762582-Chloronicotinic acid

Product 1

HCID 819931Methyl 2-chloronicotinate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloronicotinic acid (2.00 g, 12.69 mmol) in DMF (40 mL) at 0° C. is added cesium carbonate (4.96 g, 15.23 mmol) followed by iodomethane (0.95 mL, 15.23 mmol). The reaction mixture is warmed to room temperature and stirred 16 h. Dilution with ethyl acetate is followed by washing with water, 8% NaHCO3 solution and brine. The organic layer is dried (MgSO44) and concentrated under reduced pressure to give 2-chloronicotinic acid methyl ester as an oil: 1H NMR (CDCl3, 300 MHz): δ 8.55 (1H, dd), 8.18 (1H, dd), 7.33 (1H, dd), 3.97 (3H, s).

Workup

  1. washby washing with water, 8% NaHCO3 solution and brine
  2. customThe organic layer is dried (MgSO44)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40df8c39973a4a82abc34e8c191a2709
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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