Dimethylformamide → 3-Chloroquinoxalin-2-amine

HRID 331179Notes

Reaction equation

HRID 331179 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[N:14](C=O)C>O>[Cl:1][C:2]1[C:11]([NH2:14])=[N:10][C:9]2[C:4]([N:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 166592,3-Dichloroquinoxaline

Product 1

HCID 8172743-Chloroquinoxalin-2-amineYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2,3-dichloroquinoxaline (4 g, 20 mmol, commercially available from Aldrich) is dissolved in dry DMF (20 ml) and treated with solid (NH4)2CO3 (9.7 g, 101 mmol). The resulting mixture is stirred at 60° C. for 3 days (reaction showed 60% completion). The reaction mixture is diluted with water and the product is extracted with EtOAc. The organic layer is dried and the solvent was removed under reduced pressure. The crude residue obtained is purified via column chromatography by eluting with petroleum ether: EtOAc to afford 1.9 g (53%) of the title compound as a pale yellow solid. LC/MS: (ES+): 180.1.

Workup

  1. custom(reaction showed 60% completion)
  2. extractionthe product is extracted with EtOAc
  3. customThe organic layer is dried
  4. customthe solvent was removed under reduced pressure
  5. customThe crude residue obtained
  6. customis purified via column chromatography
  7. washby eluting with petroleum ether

Sources & evidence

ORD record
ord-918fffcbf03649adbd0ba0a417278d50
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Reaction notes

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