Oxalic Acid → 1,4,7,8,9,10-Hexahydropyrido[3,4-f]quinoxaline-2,3-dione

HRID 1106438Notes

Reaction equation

HRID 1106438 reaction equation
Cl.Br.[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:14])[C:11]=2[NH2:13])[CH2:6][CH2:5][NH:4]1.[C:15](O)(=[O:19])[C:16](O)=[O:17]>Cl>[NH:13]1[C:11]2[C:12]3[CH2:3][NH:4][CH2:5][CH2:6][C:7]=3[CH:8]=[CH:9][C:10]=2[NH:14][C:16](=[O:17])[C:15]1=[O:19]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 21253068HCID 21253068, compound

Product 1

HCID 212530731,4,7,8,9,10-Hexahydropyrido[3,4-f]quinoxaline-2,3-dioneYield 81.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 29 (01.27 g, 0.96 mmol) in 25 mL 3 N HCl, was treated with oxalic acid (0.15 g, 1.2 mmol) and heated at reflux for 4 h. The mixture was cooled in an ice bath and the precipitate collected by filtration and washed with 3 N HCl, water and then diethyl ether consecutively. After air drying, the solid was suspended in 10 mL water and heated at approximately 90° C., basifyed with ammonium hydroxide solution to pH 8, and filtered hot. The solid was washed first with water, then with diethyl ether and then dried in a vacuum oven to give an off-white solid (0.17 g, 81% yield) mp=294-297° C. MS (CI) M+1, 218; IR 1691, 1659 cm-1.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h
  3. temperatureThe mixture was cooled in an ice bath
  4. filtrationthe precipitate collected by filtration
  5. washwashed with 3 N HCl, water
  6. customAfter air drying
  7. filtrationfiltered hot
  8. washThe solid was washed first with water
  9. dry with materialwith diethyl ether and then dried in a vacuum oven

Sources & evidence

ORD record
ord-7cab29ee313f4587b569f9c18f628e3a
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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