Hydrochloric Acid → 6,7-Dichloro-5-(4-pyridyl)-2,3(1H,4H)-quinoxalinedione

HRID 842657Notes

Reaction equation

HRID 842657 reaction equation
[Cl:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13]C)[C:6]([O:15]C)=[N:5]2.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6](=[O:15])[NH:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 108606436,7-Dichloro-2,3-dimethoxy-5-(4-pyridyl)quinoxaline

Product 1

HCID 110667836,7-Dichloro-5-(4-pyridyl)-2,3(1H,4H)-quinoxalinedioneYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6,7-dichloro-2,3-dimethoxy-5-(4-pyridyl)quinoxaline (Preparation 2, 110 mg, 0.327 mmol), 2M aqueous hydrochloric acid solution (1 mL) and 1,4-dioxane (7 ml) was heated under reflux for 2 hours, cooled, and concentrated under reduced pressure. The solid residue was triturated with water, collected by filtration and washed with water and diethyl ether to give the title compound (17 mg, 17%) as a white solid, mp >300° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. customThe solid residue was triturated with water
  6. filtrationcollected by filtration
  7. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-877203458497448cb537e1c25866f628
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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