Ethyl Acetate → 2-(Bromomethyl)-3-(2-chlorophenyl)-5-nitroquinoxaline

HRID 216869

Reaction equation

HRID 216869 reaction equation
[Br:1][CH2:2][C:3](=O)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=O.C(OCC)(=O)C.[N+:20]([C:23]1[C:24]([NH2:30])=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21]>>[Br:1][CH2:2][C:3]1[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[Cl:12])=[N:30][C:24]2[C:25](=[CH:26][CH:27]=[CH:28][C:23]=2[N+:20]([O-:22])=[O:21])[N:29]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 43595253-Nitro-1,2-phenylenediamineHCID 575561703-Bromo-1-(2-chlorophenyl)propane-1,2-dione

Product 1

HCID 577078072-(Bromomethyl)-3-(2-chlorophenyl)-5-nitroquinoxaline

Procedure

To a solution of 3-bromo-1-(2-chlorophenyl)propane-1,2-dione (Prepared in Example 81, 4.2971 g, 16.4325 mmol) in ethyl acetate (109.55 mL, 16.433 mmol) was added 3-nitro-1,2-phenylenediamine (2.5165 g, 16.433 mmol) at room temperature and the resulting red mixture was stirred at room temperature. After 26 h of stirring at room temperature, the mixture was concentrated under reduced pressure to give 2-(bromomethyl)-3-(2-chlorophenyl)-5-nitroquinoxaline including its regioisomer as a red syrup: LC-MS (ESI) m/z 378.0 and 379.9 [M+H]+. The crude product as a red syrup was carried on crude without purification for the next step.

Workup

  1. stirringAfter 26 h of stirring at room temperature
  2. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd846b3575064eebb1e7b34bb85f63af
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Linked notes

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