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

HRID 1477358Notes

Reaction equation

HRID 1477358 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-760f83a3f0814ae5b1956411cc7da3ba
Source dataset
uspto-grants-2016_08
Patent number
US09403797B2

Reaction notes

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