Methanol → Methyl 2,5-Dichloronicotinate

HRID 1870299Notes

Reaction equation

HRID 1870299 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:12][OH:13]>>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([O:13][CH3:12])=[O:5]

Participants

3

Reactant 2

HCID 887MethanolHCID 27999962,5-Dichloro-nicotinoyl chloride

Product 1

HCID 2764318Methyl 2,5-DichloronicotinateYield 86%

Procedure

2,5-dichloronicotinic acid chloride (5.0 g) was dissolved in methanol (30 ml) with stirring under ice cooling and then stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure and the residue was dissolved in ether and washed with saturated sodium hydrogen carbonate water solution and brine. The extract was dried over anhydrous magnesium sulphate and filtered. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (30/1), to give the title compound (4.2 g, 86%).

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ether
  4. washwashed with saturated sodium hydrogen carbonate water solution and brine
  5. dry with materialThe extract was dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (30/1)

Sources & evidence

ORD record
ord-3f77928dd3f34282a8f705eac3fe1b27
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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