Water → HCID 85851272, compound

HRID 2039599Notes

Reaction equation

HRID 2039599 reaction equation
C(O[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[C:16]([O:18]CC)=[O:17])[N:12]=[CH:11][CH:10]=[N:9]2)=[O:5])C.[OH-].[K+].O>O1CCOCC1.CC(OC(C)=O)=O>[N:9]1[C:8]2[CH:7]=[C:6]3[C:4](=[O:5])[O:18][C:16](=[O:17])[C:15]3=[CH:14][C:13]=2[N:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 57855907HCID 57855907, compound

Product 1

HCID 85851272HCID 85851272, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 312751,4-DioxaneSolvent

Procedure

11.8 g (43.0 mmol) quinoxaline-6,7-dicarboxylic acid diethyl ester and 5.0 g (86 mmol) KOH dissolved in 100 ml dioxane and 50 ml water is stirred at ambient temperature during 20 hours. After evaporation of the dioxane, the solution is made slightly acidic (pH ˜5) with HCl 2N and is extracted with methylene chloride. After evaporation of the organic phase, 6.6 g diacide is isolated. This product is directly dissolved in 25 ml acetanhydride and heated at reflux during 8 hours. Acetanhydride is evaporated and 6.2 g furo[3,4-g]quinoxaline-6,8-dione is isolated. Without purification, this material is dissolved in 50 ml methanol and heated at reflux during 1 hour. After evaporation of the solvent, the residue is crystallised in diisopropyl ether to give 6.25 g of the title compound (63%): 1H-NMR (DMSO-d6, 400 MHz): 3.73 ppm (s, 3H), 8.20 (s, 1H), 8.35 (s, 1H), 9.0 (2 s, 2H), 13.6 (s, b, 1H).

Workup

  1. customAfter evaporation of the dioxane
  2. extractionis extracted with methylene chloride
  3. customAfter evaporation of the organic phase
  4. custom6.6 g diacide is isolated
  5. temperatureheated
  6. temperatureat reflux during 8 hours
  7. customAcetanhydride is evaporated

Sources & evidence

ORD record
ord-e289138931e54865bf70ed771300da47
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

Loading…