Acetic Acid → HCID 178492031, compound

HRID 1387671Notes

Reaction equation

HRID 1387671 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:21](=[O:22])[C:12]3=[CH:13][NH:14][C:15]4[C:20]([N:11]3[C:10]2=[O:23])=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:5][CH:4]=1.[Br:24]Br.C(O)(=O)C.CO.C(Cl)Cl>O1CCOCC1.[Zn]>[Br:24][C:18]1[CH:19]=[C:20]2[C:15]([NH:14][CH:13]=[C:12]3[C:21](=[O:22])[N:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[C:10](=[O:23])[N:11]32)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 21226129Dichloromethane methanolHCID 178492032HCID 178492032, compound

Product 1

HCID 178492031HCID 178492031, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 2-(4-Methoxyphenyl)-imidazo[1,5,a]quinoxaline-1,3(2H,5H)-dione (100 mg) in anhydrous dioxane (4mL) was added bromine (200 mg). The reaction was stirred at 20° C. for 15 min, and was then poured directly into boiling acetic acid (50 mL) containing zinc powder (500 mg). The reaction was refluxed for 5 min and allowed to cool to room temperature. After dilution with 10% methanol/methylene chloride (100 mL). the mixture was filtered through silica gel, the solvent was removed in vacuo, and the resulting solid was treated with boiling ethanol (25 mL) followed by dilution with water (100 mL). The mixture was cooled to 0° C. and the solid was filtered and dried to yield 8-Bromo-2-(4-methoxyphenyl)-imidazo[1,5,a]quinoxaline-1,3(2H,5H)-dione (Compound 33) as a yellow solid. m.p. 154° (dec).

Workup

  1. additionwas then poured directly
  2. temperatureThe reaction was refluxed for 5 min
  3. temperatureto cool to room temperature
  4. filtrationthe mixture was filtered through silica gel
  5. customthe solvent was removed in vacuo
  6. additionthe resulting solid was treated with boiling ethanol (25 mL)
  7. temperatureThe mixture was cooled to 0° C.
  8. filtrationthe solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-cde70fe4f0ec45b7bb7e46803e16cd6b
Source dataset
uspto-grants-2001_07
Patent number
US06268496B1

Reaction notes

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