Methanol → 2-(Methoxycarbonyl)pyridine-4-carboxylic acid

HRID 1838242Notes

Reaction equation

HRID 1838242 reaction equation
S(=O)(=O)(O)O.[N:6]1[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][C:7]=1[C:15]([OH:17])=[O:16].[CH3:18]O>>[CH3:18][O:16][C:15]([C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][N:6]=1)[C:12]([OH:14])=[O:13])=[O:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 103652,4-Pyridinedicarboxylic acid

Product 1

HCID 187533102-(Methoxycarbonyl)pyridine-4-carboxylic acid

Conditions

Temperature
5 °C

Procedure

A 1.7 ml portion of concentrated sulfuric acid was added to 50 ml of methanol solution containing 5.0 g of pyridine-2,4-dicarboxylic acid, and the mixture was heated under reflux for 1 hour and 10 minutes. After cooling, this was poured into ice water and stirred at 5° C. for 3 hours, and the thus precipitated white solid was collected by filtration. A 5.7 g portion of this product was dissolved in 100 ml of methanol with heating, and the solution was cooled and then stirred at room temperature. By collecting the thus precipitated white solid by filtration, 2.5 g of the title compound was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour and 10 minutes
  3. temperatureAfter cooling
  4. filtrationthe thus precipitated white solid was collected by filtration
  5. dissolutionA 5.7 g portion of this product was dissolved in 100 ml of methanol
  6. temperaturewith heating
  7. temperaturethe solution was cooled
  8. stirringstirred at room temperature
  9. customBy collecting the thus precipitated white solid
  10. filtrationby filtration

Sources & evidence

ORD record
ord-2faf7a35497c46e2877df3934cd2ac4a
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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