Acetic Anhydride → 3-Propylfuro[3,4-b]pyridine-5,7-dione

HRID 1253272Notes

Reaction equation

HRID 1253272 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=1)[CH2:2][CH3:3].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:13](=[O:14])[O:15][C:10](=[O:12])[C:7]2=[N:8][CH:9]=1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 14028767HCID 14028767, compound

Product 1

HCID 140287683-Propylfuro[3,4-b]pyridine-5,7-dione

Procedure

2 g of 5-propylpyridine-2,3-dicarboxylic acid together with 25 ml of acetic anhydride and 2 g of anhydrous sodium acetate are heated for 1 hour at 70° C. After removal of the acetic anhydride by evaporation, the residue is partitioned between water and chloroform and the organic phase is dried over MgSO4 and then concentrated by evaporation. The residue is crystallised from ether/hexane, affording 5-propylpyridine-2,3-dicarboxylic anhydride with a melting point of 42°-44° C.

Workup

  1. customAfter removal of the acetic anhydride
  2. customby evaporation
  3. customthe residue is partitioned between water and chloroform
  4. dry with materialthe organic phase is dried over MgSO4
  5. concentrationconcentrated by evaporation
  6. customThe residue is crystallised from ether/hexane

Sources & evidence

ORD record
ord-6201b157ea9547cd895a42bb6f66aebd
Source dataset
uspto-grants-1988_05
Patent number
US04748244

Reaction notes

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