Trifluoroacetic acid → 6-chloroquinoxaline-2,3-dicarbonitrile

HRID 1377933Notes

Reaction equation

HRID 1377933 reaction equation
[NH:1]=[C:2]([C:7]#[N:8])[C:3](=[NH:6])[C:4]#[N:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13](N)=[C:12](N)[CH:11]=1.FC(F)(F)C(O)=O>O>[Cl:9][C:10]1[CH:11]=[C:12]2[C:13](=[CH:14][CH:15]=1)[N:6]=[C:3]([C:4]#[N:5])[C:2]([C:7]#[N:8])=[N:1]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 72634-Chloro-1,2-diaminobenzeneHCID 119924Diiminobutanedinitrile

Product 1

HCID 3038656-chloroquinoxaline-2,3-dicarbonitrileYield 59.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.5 g (4.7 mmols) of the diiminosuccinonitrile and 0.67 g (4.7 mmols) of 4-chloro-1,2-phenylenediamine was slowly added to 10 ml of trifluoroacetic acid at about 20° C. over a period of 30 minutes, and the resulting mixture was stirred at room temperature for 8 hours and then allowed to stand overnight. To the reaction mixture was added 50 ml water, and the solid precipitated was filtered and sufficiently washed with water. The solid thus obtained was dried under reduced pressure, followed by a silica gel column chromatography (eluent: hexane/ethyl acetate=75/25) and then recrystallization from chloroform/ethanol, whereby 0.6 g (59%) of 6-chloro-2,3-dicyanoquinoxaline was obtained as colorless crystals.

Workup

  1. waitto stand overnight
  2. customthe solid precipitated
  3. filtrationwas filtered
  4. washsufficiently washed with water
  5. customThe solid thus obtained
  6. customwas dried under reduced pressure
  7. customrecrystallization from chloroform/ethanol

Sources & evidence

ORD record
ord-0cb6c80ab55b44c3b9a90a2e23c200e5
Source dataset
uspto-grants-1997_09
Patent number
US05665875

Reaction notes

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