Methanol → 2,3-Dimethyl 2,3-pyridinedicarboxylate

HRID 2174685

Reaction equation

HRID 2174685 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=[O:8])[C:2]=1[C:10]([OH:12])=O.S(=O)(=O)(O)O.[C:18](=O)([O-])[O-].[Na+].[Na+].[CH3:24][OH:25]>>[CH3:24][O:25][C:10]([C:2]1[C:3]([C:7]([O:9][CH3:18])=[O:8])=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:12]

Participants

5

Reactant 4

HCID 887MethanolHCID 1066Quinolinic AcidHCID 1118Sulfuric AcidHCID 10340Sodium Carbonate

Product 1

HCID 690582,3-Dimethyl 2,3-pyridinedicarboxylate

Procedure

To a solution of pyridine-2,3-dicarboxylic acid (50.0 g, 0.299 mol) in methanol (500 ml) was added con. sulfuric acid (20 ml). After heated to reflux for 24 hours, the mixture was basified with saturate sodium carbonate solution until pH=8 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulphate, filtered and evaporated to give D78 (45.7 g) as a white solid.

Workup

  1. temperatureAfter heated
  2. temperatureto reflux for 24 hours
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give D78 (45.7 g) as a white solid

Sources & evidence

ORD record
ord-3b19b6432f254ab399d3b17d25803d23
Source dataset
uspto-grants-2015_06
Patent number
US09062033B2

Linked notes

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