Methanol → Methyl 2-chloro-6-methoxyisonicotinate

HRID 559674Notes

Reaction equation

HRID 559674 reaction equation
[CH3:1][OH:2].[H-].[Na+].[CH3:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12](Cl)[N:11]=[C:10]([Cl:15])[CH:9]=1>C1COCC1.[Cl-].[NH4+]>[CH3:5][O:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([O:2][CH3:1])[N:11]=[C:10]([Cl:15])[CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 93237Methyl 2,6-dichloroisonicotinate

Product 1

HCID 13339618Methyl 2-chloro-6-methoxyisonicotinate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of dry methanol (2.2 mL, 53 mmol) in THF (200 mL) was added sodium hydride (2.12 g, 53 mmol) in portions under a stream of nitrogen. When gas evolution ceased, 2,6-dichloro-isonicotinic acid methyl ester (10.0 g, 48.5 mmol) was added. After stirring for 2 hours, the reaction was diluted with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (4×50 mL). The combined organics were washed with brine, dried over sodium sulfate, and concentrated to afford 2-chloro-6-methoxy-isonicotinic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate (4×50 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-22b412909e3a4838953bbd1eb09163e4
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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