4-Chloro-1,2-diaminobenzene → 6-Chloroquinoxaline-2,3-diamine

HRID 2397543Notes

Reaction equation

HRID 2397543 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1>CO.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]=[C:5]([NH2:8])[C:4]([NH2:9])=[N:9]2

Participants

4

Reactant 1

HCID 72634-Chloro-1,2-diaminobenzene

Product 1

HCID 125173906-Chloroquinoxaline-2,3-diamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of dimethyl oxaldiimidate (48 parts) in methanol (80 parts) was added to a slurry of 4-chloro-o-phenylenediamine (56 parts) in 0.3% aqueous hydrochloric acid (60 parts). The temperature rose to 54°. The reaction mixture was cooled and filtered to give a brown solid. After washing with THF, 61.4 parts of tan solid remained (80%). Recrystallization from THF or dioxane gave light-yellow crystals of 6-chloro-2,3-diaminoquinoxaline, m.p. 300°-303°.

Workup

  1. customrose to 54°
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customto give a brown solid
  5. washAfter washing with THF, 61.4 parts of tan solid
  6. customRecrystallization from THF or dioxane

Sources & evidence

ORD record
ord-be26498c628e495083b1eb1bcc21f185
Source dataset
uspto-grants-1977_05
Patent number
US04022777

Reaction notes

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