Methanol → Methyl 2-chloro-6-methoxynicotinate

HRID 533138Notes

Reaction equation

HRID 533138 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:13][OH:14]>>[CH3:13][O:14][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[N:10][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 887MethanolHCID 86667500HCID 86667500, compound

Product 1

HCID 10584232Methyl 2-chloro-6-methoxynicotinateYield 90%

Procedure

A mixture of 2-chloro-6-methoxy-nicotinoyl chloride (340 g, 1650 mmol) in MeOH (4500 mL) was stirred at RT for 1 h. The solvent was evaporated in vacuo. The mixture was basified with a saturated solution of NaHCO3 and extracted with EtOAc. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; petroleum ether/EtOAc 10/1). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-chloro-6-methoxy-nicotinic acid methyl ester (280 g, 90%) as a solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography (silica; petroleum ether/EtOAc 10/1)
  8. customThe desired fractions were collected
  9. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-9704188e9fee4de7865ed390d03f2258
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

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