2,3-Dichloroquinoxaline → HCID 10754331, compound

HRID 1954700Notes

Reaction equation

HRID 1954700 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17]>C(O)C>[Cl:12][C:11]1[C:2]([NH:17][CH2:16][CH:15]([O:18][CH3:19])[O:14][CH3:13])=[N:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 166592,3-DichloroquinoxalineHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 10754331HCID 10754331, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.0 g of 2,3-dichloroquinoxaline and 5.5 ml of aminoacetaldehyde dimethyl acetal in 75 ml of ethanol is refluxed for 4 h. After concentrating under vacuum, the resulting mixture is added with water and extracted with ethyl acetate. The organic extracts are then washed with saturated NaCl, dried and evaporated. The residue is finally chromatographed on SiO2 (eluent: CH2Cl2), thereby obtaining 5.0 g of 2-chloro-3-(2,2-dimethoxyethylamino)quinoxaline (IR (KBr): 3347, 2936, 1580, 1523, 1129 cm-1). 4.5 g of this product are then treated with 20 ml of 48% HBr and the mixture is refluxed for 4 h. After cooling down, the mixture is neutralized with aqueous NaOH and the resulting precipitate is filtered under vacuum and dried to obtain 3.2 g of imidazo[1,2-a]quinoxalin-4(5H)-one (m.p. >300° C.)

Workup

  1. temperatureis refluxed for 4 h
  2. concentrationAfter concentrating under vacuum
  3. additionthe resulting mixture is added with water
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts are then washed with saturated NaCl
  6. customdried
  7. customevaporated
  8. customThe residue is finally chromatographed on SiO2 (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-1f92f95882294cbdbdbfbeb9b03bd641
Source dataset
uspto-grants-2000_09
Patent number
US06124287

Reaction notes

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