Quinolinic Acid → Furo[3,4-b]pyridine-5,7-dione

HRID 1721281Notes

Reaction equation

HRID 1721281 reaction equation
[N:1]1[C:6]([C:7]([OH:9])=O)=[C:5]([C:10]([OH:12])=[O:11])[CH:4]=[CH:3][CH:2]=1>C(OC(=O)C)(=O)C>[N:1]1[C:6]2[C:7]([O:12][C:10](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1)=[O:9]

Participants

3

Reactant 1

HCID 1066Quinolinic Acid

Product 1

HCID 69688Furo[3,4-b]pyridine-5,7-dioneYield 97%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 2-methyloxazolo 5,4-b!pyridine-5,6-dicarboxylic acid (4.84 g, 0.0218 mol) in acetic anhydride (150 mL) is slowly heated to 70° C. at which point all the solids dissolve forming a yellow solution. The reaction mixture is heated at 70° C. overnight, cooled to room temperature, and concentrated in vacuo. Xylene is added to remove excess acetic anhydride by codistillation. 2-Methyloxazolo 5,4-b!pyridine-5,6-dicarboxylic anhydride is obtained as a pale yellow solid in 97% yield melting point 194°-196° C.

Workup

  1. additionA suspension of 2-methyloxazolo 5,4-b
  2. dissolutiondissolve
  3. customforming a yellow solution
  4. temperaturecooled to room temperature
  5. concentrationconcentrated in vacuo
  6. additionXylene is added
  7. customto remove excess acetic anhydride by codistillation

Sources & evidence

ORD record
ord-5d5576ea1a314e15a3907d731d9d3bbc
Source dataset
uspto-grants-1996_04
Patent number
US05510319

Reaction notes

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