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

HRID 1392605Notes

Reaction equation

HRID 1392605 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-4d269aeaa42b40ce893601f8fc55035f
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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