Water → Methyl 2-chloro-5-fluoro-6-methoxynicotinate

HRID 1510681Notes

Reaction equation

HRID 1510681 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C[O-].[Na+].CO.O.[C:20](OCC)(=[O:22])C>CO>[Cl:1][C:2]1[N:11]=[C:10]([O:22][CH3:20])[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2775354Methyl 2,6-dichloro-5-fluoronicotinateHCID 23694274Sodium methanolate methanol

Product 1

HCID 40148026Methyl 2-chloro-5-fluoro-6-methoxynicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.5 g of methyl 2,6-dichloro-5-fluoronicotinate in 12 mL of methanol, a solution of 1.3 g of 28% sodium methoxide/methanol in 3 mL of methanol was dropped, and the mixture was stirred at room temperature for 40 minutes. Thereto were added water and ethyl acetate, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.2 g of methyl 2-chloro-5-fluoro-6-methoxynicotinate as a white solid.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washthe resultant solution was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4cda4a63888c4641b2b2a84dccf1ae56
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

Loading…