Methyl4,6-dichloronicotinate → Methyl 6-chloro-4-methoxypyridine-3-carboxylate

HRID 251574Notes

Reaction equation

HRID 251574 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9](Cl)=[CH:8][C:7]([Cl:11])=[N:6][CH:5]=1.[CH3:13][O-:14].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([O:14][CH3:13])=[CH:8][C:7]([Cl:11])=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 2764083Methyl4,6-dichloronicotinateHCID 10942334Sodium Methoxide

Product 1

HCID 22498691Methyl 6-chloro-4-methoxypyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4,6-dichloro-nicotinic acid methyl ester (6.0 g, 29 mmol), NaOMe (2.0 g, 37 mmol) in THF (60 mL) is stirred overnight at room temperature. The solvent is removed in vacuo. Ice-cold dilute HCl solution is added to the solution. The mixture is neutralized with NaHCO3 and extracted with EtOAc. The extract is washed with water, dried, and concentrated. The residue is triturated with hexane until solid is formed. The solid is collected by filtration to give 6-chloro-4-methoxy-nicotinic acid methyl ester. 1H NMR (CDCl3) 8.72 (s, 1H), 6.91 (s, 1H), 3.97 (s, 3H), 3.90 (s, 3H).

Workup

  1. customThe solvent is removed in vacuo
  2. additionIce-cold dilute HCl solution is added to the solution
  3. extractionextracted with EtOAc
  4. washThe extract is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is triturated with hexane until solid
  8. customis formed
  9. filtrationThe solid is collected by filtration

Sources & evidence

ORD record
ord-23bf8aeeafff44c2854c66758f793103
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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