Stannous Chloride → 6-Amino-5-chloro-7-trifluoromethyl-1,4-dihydroquinoxaline-2,3-dione

HRID 439479Notes

Reaction equation

HRID 439479 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=[O:20])[C:6](=[O:19])[NH:7]2.Cl[Sn]Cl>CCO>[NH2:12][C:11]1[C:2]([Cl:1])=[C:3]2[C:8](=[CH:9][C:10]=1[C:15]([F:17])([F:18])[F:16])[NH:7][C:6](=[O:19])[C:5](=[O:20])[NH:4]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 105668755-Chloro-6-nitro-7-trifluoromethyl-1,4-dihydroquinoxaline-2,3-dione

Product 1

HCID 107790786-Amino-5-chloro-7-trifluoromethyl-1,4-dihydroquinoxaline-2,3-dioneYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-chloro-6-nitro-7-trifluoromethyl-1,4-dihydroquinoxaline-2,3-dione (230 mg, 0.743 mmol), SnCl2 ·2H2O (1.90 g, 7.43 mmol) and EtOH (300 mL) was refluxed for 24 h, then rota-evaporated to dryness. The residual solid was washed on a Bursch funnel with water (6×15 mL), and dried to give 153 mg (74%) of the title compound as a yellow powder. Mp>360° C. (1H NMR (DMSO-d6) 11.777 (s, 1H), 11.360 (s, 1H), 7.140 (s, 1H), 5.499 (s, 2H).

Workup

  1. temperaturewas refluxed for 24 h
  2. customrota-evaporated to dryness
  3. washThe residual solid was washed on a Bursch funnel with water (6×15 mL)
  4. customdried

Sources & evidence

ORD record
ord-b24d884310134a1b964f1a2977501874
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

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