Furo[3,4-b]pyridine-5,7-dione → HCID 13246848, compound

HRID 1650087Notes

Reaction equation

HRID 1650087 reaction equation
[N:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]([O:5][C:6]2=[O:11])=O.[NH2:12][C:13]([CH3:19])([CH:16]([CH3:18])[CH3:17])[C:14]#[N:15]>C(Cl)Cl>[CH:16]([C:13]([CH3:19])([N:12]1[C:6](=[O:11])[C:7]2[C:2](=[N:1][CH:10]=[CH:9][CH:8]=2)[C:3]1=[O:5])[C:14]#[N:15])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 943552-Amino-2,3-dimethylbutyronitrile

Product 1

HCID 13246848HCID 13246848, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution containing 212 g quinolinic anhydride in 950 ml methylene chloride is added to a moderate rate 167 g of 2-amino-2,3-dimethylbutyronitrile. The mixture had reached the boiling point of the solution after about one quarter of the aminonitrile had been added and the rate of addition is adjusted to maintain this temperature. After the addition the solution is heated under reflux for a further 4 hours. The solution is cooled, filtered and concentrated to a thick oil. This oil is dissolved in 950 ml acetic anhydride, 6 g anhydrous sodium acetate added and the mixture distilled until the vapor temperature reached 118° C. when the heating was continued under reflux for 3 hours. The mixture is concentrated in vacuo the residue dissolved in 500 ml toluene and again concentrated. This is repeated. The residue is slurried with a mixture of ether and hexane and the crude product which crystallizes collected (349 g). This is dissolved in 700 ml methylene chloride and filtered through a column containing 700 g silica gel and the product eluted with methylene chloride. Concentration of the eluant gave 258 g of the desired product. An analytically pure sample with mp 95°-96° C. can be obtained by the recrystallization of the product from ether-methylene chloride.

Workup

  1. additionhad been added
  2. additionthe rate of addition
  3. temperatureto maintain this temperature
  4. additionAfter the addition the solution
  5. temperatureis heated
  6. temperatureunder reflux for a further 4 hours
  7. temperatureThe solution is cooled
  8. filtrationfiltered
  9. concentrationconcentrated to a thick oil
  10. dissolutionThis oil is dissolved in 950 ml acetic anhydride
  11. addition6 g anhydrous sodium acetate added
  12. distillationthe mixture distilled until the vapor temperature
  13. customreached 118° C.
  14. temperatureunder reflux for 3 hours
  15. concentrationThe mixture is concentrated in vacuo the residue
  16. dissolutiondissolved in 500 ml toluene
  17. concentrationagain concentrated
  18. additionThe residue is slurried with a mixture of ether and hexane
  19. customthe crude product which crystallizes
  20. customcollected (349 g)
  21. dissolutionThis is dissolved in 700 ml methylene chloride
  22. filtrationfiltered through a column
  23. additioncontaining 700 g silica gel
  24. washthe product eluted with methylene chloride

Sources & evidence

ORD record
ord-3dba7ded2ed9495a89f7f3c8a9c7d3c9
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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