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

HRID 2102764Notes

Reaction equation

HRID 2102764 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=[CH:3][C:2]=1[C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.O.[CH3:19]O>>[CH3:19][O:11][C:10]([C:2]1[CH:3]=[CH:4][C:5]([C:7]([OH:9])=[O:8])=[CH:6][N:1]=1)=[O:12]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 74932,5-Pyridinedicarboxylic acid

Product 1

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

Procedure

To a suspension of pyridine-2,5-dicarboxylic acid (4.2 g, 25.1 mmol) (Aldrich) in methanol (50 mL) was added concentrated sulfuric acid (1.5 g, 15.3 mmol) (Aldrich). The mixture was heated at refluxing for 2 hours. The crude was cooled down to room temperature and poured into water (250 mL). The precipitate formed was collected and washed with methanol to give pyridine-2,5-dicarboxylic acid-2-methyl ester as a grey solid. (Yield 1.5 g, 33%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat refluxing for 2 hours
  3. customThe precipitate formed
  4. customwas collected
  5. washwashed with methanol

Sources & evidence

ORD record
ord-df8ccfff82e249c8bc3ded56744f8d72
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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