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

HRID 1054202Notes

Reaction equation

HRID 1054202 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=O)[C:2]=1[C:10]([OH:12])=[O:11].C(OC(=O)C)(=O)C>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=[O:9])[O:12][C:10](=[O:11])[C:2]=12

Participants

3

Reactant 2

HCID 1066Quinolinic AcidHCID 7918Acetic Anhydride

Product 1

HCID 69688Furo[3,4-b]pyridine-5,7-dioneYield 86.7%

Conditions

Temperature
115 °C

Procedure

A mixture of pyridine-2,3-dicarboxylic acid (2 g, 12 mmol) and acetic anhydride was heated at 115° C. for 4 h. Excess reagent was removed under reduced pressure. The remaining solid was triturated with hot carbon tetrachloride. After cooling, the solid was collected by vacuum filtration and dried overnight under vacuum at 60° C. to give furo[3,4-b]pyridine-5,7-dione (1.55 g, 10.4 mmol). 1H NMR (400 MHz, DMSO-d6) δ 9.10 (dd, J=4.9, 1.5 Hz, 1H), 8.50 (dd, J=7.8, 1.5 Hz, 1H), 7.90 (dd, J=7.8, 4.9 Hz, 1H).

Workup

  1. customExcess reagent was removed under reduced pressure
  2. customThe remaining solid was triturated with hot carbon tetrachloride
  3. temperatureAfter cooling
  4. filtrationthe solid was collected by vacuum filtration
  5. customdried overnight under vacuum at 60° C.

Sources & evidence

ORD record
ord-81551d410b3d4519b770d25cab2af8ed
Source dataset
uspto-grants-2016_07
Patent number
US09394299B2

Reaction notes

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