Methanol → Methyl 2-chloro-6-methoxyisonicotinate

HRID 732407Notes

Reaction equation

HRID 732407 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[N:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([O:11][CH3:12])[N:10]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27821242-Chloro-6-methoxypyridine-4-carboxylic acid

Product 1

HCID 13339618Methyl 2-chloro-6-methoxyisonicotinate

Procedure

Mix commercially available 2-chloro-6-methoxy-isonicotinic acid (17 g, 90.6 mmol), concentrated sulfuric acid (0.85 mL) in methanol (150 mL) and reflux overnight. Cool the mixture to room temperature, filter and dry the solid under vacuum to give the title compound (15.5 g). Concentrate filtrate and dilute with ethyl acetate (150 mL). Wash with sodium bicarbonate solution, water, dry (sodium sulfate) and concentrate to give additional title compound (1.7 g) (17.2 g, 93% combined yield).

Workup

  1. temperaturereflux overnight
  2. filtrationfilter
  3. customdry the solid under vacuum

Sources & evidence

ORD record
ord-54369f18103945da97ca1f5f8227fed3
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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