Methanol → Methyl 2-chloro-6-methoxyisonicotinate

HRID 1436551Notes

Reaction equation

HRID 1436551 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-bfcf5995e6924cc5b64763fecdd7aaae
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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