Methanol → 6-(Methoxycarbonyl)pyridine-3-carboxylic acid

HRID 1680453Notes

Reaction equation

HRID 1680453 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=1)([OH:3])=[O:2].[CH3:13]O>S(=O)(=O)(O)O.O>[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=1)([O:3][CH3:13])=[O:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 74932,5-Pyridinedicarboxylic acid

Product 1

HCID 5796316-(Methoxycarbonyl)pyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

The starting material is prepared as follows: The suspension of 3,000 g at 6-carboxy-nicotinic acid in 18,000 ml of methanol and 300 ml of concentrated sulfuric acid is refluxed for 3 hours while stirring under nitrogen. The solution formed is cooled to 5°, diluted with 18,000 ml of water, the resulting suspension stirred for 1 hour at 5°, the precipitate collected and washed with 4,000 ml of water, to yield the 6-carbomethoxynicotinic acid melting at 195°-202°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for 3 hours
  3. customThe solution formed
  4. temperatureis cooled to 5°
  5. stirringthe resulting suspension stirred for 1 hour at 5°
  6. customthe precipitate collected
  7. washwashed with 4,000 ml of water

Sources & evidence

ORD record
ord-33e43164f5854409b04fe3ca1e50ca5a
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

Loading…