Ammonia → 2-Aminoquinoxaline

HRID 971630Notes

Reaction equation

HRID 971630 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:12]>CS(C)=O>[NH2:12][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2389382-Chloroquinoxaline

Product 1

HCID 2245732-Aminoquinoxaline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Three g. of 2-chloroquinoxaline (commercially available) was dissolved in 50 ml. of dimethylsulfoxide and heated on the steam bath while anhydrous ammonia was bubbled into the mixture. The mixture was heated and stirred overnight on the steam bath. It was poured into 150 ml. of a mixture of ice and water, and the solid which precipitated was collected by filtration. This solid was recovered starting material and was discarded. The filtrate was cooled in an ice bath and the solid which precipitated was filtered off. This solid was identified by infrared spectrum as the desired compound, 2-aminoquinoxaline. It was used as is without further purification.

Workup

  1. customwas bubbled into the mixture
  2. temperatureThe mixture was heated
  3. additionIt was poured into 150 ml
  4. additionof a mixture of ice and water
  5. customthe solid which precipitated
  6. filtrationwas collected by filtration
  7. customThis solid was recovered
  8. temperatureThe filtrate was cooled in an ice bath
  9. customthe solid which precipitated
  10. filtrationwas filtered off
  11. customas is without further purification

Sources & evidence

ORD record
ord-21df5d6eef3f4d92b5e7df320256e793
Source dataset
uspto-grants-1979_07
Patent number
US04160834

Reaction notes

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