Stannous Chloride → 8-Amino-5-chloro-7-Trifluoromethyl-1,4-dihydroquinoxaline-2,3-dione

HRID 439480Notes

Reaction equation

HRID 439480 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9]([N+:16]([O-])=O)=[C:8]2[C:3]=1[NH:4][C:5](=[O:20])[C:6](=[O:19])[NH:7]2.Cl[Sn]Cl>CCO>[NH2:16][C:9]1[C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][C:2]([Cl:1])=[C:3]2[C:8]=1[NH:7][C:6](=[O:19])[C:5](=[O:20])[NH:4]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 106863435-Chloro-8-nitro-7-trifluoromethyl-1,4-dihydroquinoxaline-2,3-dione

Product 1

HCID 108026568-Amino-5-chloro-7-Trifluoromethyl-1,4-dihydroquinoxaline-2,3-dioneYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5-chloro-8-nitro-7-trifluoromethyl-1,4-dihydroquinoxaline-2,3-dione (25 mg, 0.08 mmol), SnCl2 ·2H2O (97 mg, 0.34 mmol) and EtOH (3 mL) was heated at 75° C. with stirring for 12 h. Work-up as above gave 21 mg (93%) of the title compound as a yellow powder. Mp>360° C. 1H NMR (DMSO-d6) 11.441 (s, 1H), 11.324 (s, 1H), 7.241 (s, 1H), 5.916 (s, 2H).

Sources & evidence

ORD record
ord-e0dbc3f01e4f402ca569eb2d8d4c9d8f
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

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