Methyl iodide → Methyl 2-chloronicotinate

HRID 1531279Notes

Reaction equation

HRID 1531279 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 (MgSO4) 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. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca4e29198df946bb830a139fda5347ad
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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