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

HRID 576894

Reaction equation

HRID 576894 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=[C:7]([Cl:15])[CH:6]=1>C1COCC1>[Cl:15][C:7]1[CH:6]=[C:5]([O:2][CH3:1])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 2764083Methyl4,6-dichloronicotinateHCID 10942334Sodium Methoxide

Product 1

HCID 22498691Methyl 6-chloro-4-methoxypyridine-3-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide powder (0.136 g, 2.52 mmol) was added slowly to a stirred solution of methyl 4,6-dichloronicotinate (0.40 g, 1.94 mmol) in THF (4 mL) at room temperature. The reaction mixture was stirred at room temperature for 18 hours, then concentrated in vacuo onto silica gel. Gradient chromatography, eluting with 5% EtOAc:c-Hex over 5 column volume and 5-50% over 15 column volume, gave methyl 6-chloro-4-methoxynicotinate (218 mg, 1.08 mmol, 56% yield) as a white crystalline solid.

Workup

  1. concentrationconcentrated in vacuo onto silica gel
  2. washGradient chromatography, eluting with 5% EtOAc

Sources & evidence

ORD record
ord-f7aef1844d6541a7a9b2d056a7db4b2b
Source dataset
uspto-grants-2015_05
Patent number
US09040540B2

Linked notes

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