Sulfuric Acid → Methyl 6-methylpyridine-2-carboxylate

HRID 1777586Notes

Reaction equation

HRID 1777586 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=1.[C:16](=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 702826-Methylpyridine-2-carboxylic acid

Product 1

HCID 73022Methyl 6-methylpyridine-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated sulfuric acid (2 mL) was added to a solution of 6-methylpicolinic acid (1.97 g; 13.65 mmol) in methanol (50 mL). The resulting mixture was heated at reflux for 22 hours. After cooling to room temperature, the solution was made alkaline by addition of an aqueous solution of sodium carbonate. The methanol was evaporated under reduced pressure, water was added and the mixture was extracted three times with dichloromethane. Combined organic layers were dried over magnesium sulfate, and concentrated under reduced pressure to give 1.81 g (88%) of methyl 6-methylpicolinate as an oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 22 hours
  3. customThe methanol was evaporated under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted three times with dichloromethane
  6. dry with materialCombined organic layers were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4863195923d74865b4d251f2c8c55963
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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