Water → 3-Chloroquinoxalin-2-amine

HRID 1186315Notes

Reaction equation

HRID 1186315 reaction equation
[Cl:1][C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[NH4+:17].[NH4+].O.C(OCC)(=O)C>CN(C)C=O>[NH2:17][C:11]1[C:2]([Cl:1])=[N:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 166592,3-DichloroquinoxalineHCID 517111Ammonium Carbonate

Product 1

HCID 8172743-Chloroquinoxalin-2-amineYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2,3-Dichloroquinoxaline (9.90 g, 50.0 mmol) and ammonium carbonate (24.3 g, 300 mmol) were suspended in N,N-dimethylformamide (50 mL) in a stainless steel sealed tube and the mixture was stirred at 60° C. for 72 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3). Further, slurry purification was performed using diisopropyl ether, to give 2-amino-3-chloroquinoxaline (2.41 g, yield: 27%).

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)
  5. customFurther, slurry purification

Sources & evidence

ORD record
ord-ee06123a34254d5f98abb83046bf7261
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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