4-Hydrazinylimidazo[1,2-a]quinoxaline → HCID 10797569, compound

HRID 1954701Notes

Reaction equation

HRID 1954701 reaction equation
[NH:1]([C:3]1[C:4]2[N:5]([CH:13]=[CH:14][N:15]=2)[C:6]2[C:11]([N:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)N>[Ni].O>[CH:13]1[N:5]2[C:6]3[C:11]([N:12]=[C:3]([NH2:1])[C:4]2=[N:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 1

HCID 232937004-Hydrazinylimidazo[1,2-a]quinoxaline

Product 1

HCID 10797569HCID 10797569, compoundYield 108.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A mixture of 0.17 g of 4-hydrazinoimidazo[1,2-a]quinoxaline and 3.4 ml of Raney nickel in 20 ml of water is refluxed for 1.5 h. After cooling down, the mixture is filtered on Celite, followed by washing with methanolic chloroform. The filtrate is concentrated under vacuum and extracted with ethyl acetate. The organic extracts are then washed with saturated NaCl, dried and evaporated, thereby obtaining 0.17 g of imidazo[1,2-a]quinoxalin-4-amine. M.p. (DSC)=205.3° C. (onset); IR (KBr): 3301, 3143, 1653, 1525 cm-1 ; 1 -NMR (CDCl3): δ8.0 (1H,s), 7.8÷7.45 (3H,m), 7.45÷7.2 (2H,m), 5.8 (2H,sb); UV (EtOH): λmax =229, 295, 331 nm. Elementary analysis for C10H3N4 (m.w. 184.20): calcd. C 65.21, H 4.38, N 30.42%; found C 65.48, H 4.71, N 30.10%;.

Workup

  1. temperatureis refluxed for 1.5 h
  2. temperatureAfter cooling down
  3. filtrationthe mixture is filtered on Celite
  4. washby washing with methanolic chloroform
  5. concentrationThe filtrate is concentrated under vacuum
  6. extractionextracted with ethyl acetate
  7. washThe organic extracts are then washed with saturated NaCl
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-a656ff87048840a485c8aabb5ac14c05
Source dataset
uspto-grants-2000_09
Patent number
US06124287

Reaction notes

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