Quinoline-5,6-diamine → 1,4-Dihydropyrido[3,2-f]quinoxaline-2,3-dione

HRID 48215Notes

Reaction equation

HRID 48215 reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([NH2:12])[C:7]([NH2:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.[C:14](O)(=[O:18])[C:15](O)=[O:16]>Cl>[NH:12]1[C:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:10]=3[CH:9]=[CH:8][C:7]=2[NH:11][C:15](=[O:16])[C:14]1=[O:18]

Participants

4

Reactant 2

HCID 426874Quinoline-5,6-diamineHCID 122529616153-56-6

Product 1

HCID 103759121,4-Dihydropyrido[3,2-f]quinoxaline-2,3-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 5,6-quinolinediamine (11.3 g, 0.071 mol) and oxalic acid hydrate (17.9 g, 0.142 mol) in 200 mL 2N HCl was heated at reflux for 2 hours. The solid (12.3 g, 83% yield) was collected by filtration and washed consecutively with water and ether.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours

Sources & evidence

ORD record
ord-18ce3a370f5c47b09af3e24cfb90cbdf
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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