Hydrazine hydrate (1:1) → HCID 17878070, compound

HRID 1458584Notes

Reaction equation

HRID 1458584 reaction equation
O.NN.[NH2:4][C:5]1[C:6]([O:23][CH3:24])=[N:7][C:8]2[C:13]([N:14]=1)=[C:12]([N+:15]([O-])=O)[C:11]([Cl:18])=[C:10]([C:19]([F:22])([F:21])[F:20])[CH:9]=2>C(O)C.[Ru]>[NH2:4][C:5]1[C:6]([O:23][CH3:24])=[N:7][C:8]2[C:13]([N:14]=1)=[C:12]([NH2:15])[C:11]([Cl:18])=[C:10]([C:19]([F:22])([F:20])[F:21])[CH:9]=2

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 220970373-Amino-6-chloro-7-trifluoromethyl-2-methoxy-5-nitroquinoxaline

Product 1

HCID 17878070HCID 17878070, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.34 ml, 7.0 mmol) was added to a stirred solution of 3-amino-6-chloro-7-trifluoromethyl-2-methoxy-5-nitroquinoxaline (0.55g, 1.7 mmol) in ethanol (25 ml) containing suspended 10% ruthenium-on-carbon (55 mg) under nitrogen at reflux. After 20 minutes, additional hydrazine hydrate (0.17 ml, 3.4 mmol) was added, and the mixture was stirred at reflux for 30 minutes, then allowed to stand at room temperature overnight. The mixture was filtered through Arbocel filter aid, and the filter cake was washed with ethanol and dichloromethane. The filtrate was concentrated under reduced pressure to give the title compound (0.50 g, 100%) as an off-white solid.

Workup

  1. additioncontaining
  2. temperatureat reflux
  3. temperatureat reflux for 30 minutes
  4. waitto stand at room temperature overnight
  5. filtrationThe mixture was filtered through Arbocel
  6. filtrationfilter aid
  7. washthe filter cake was washed with ethanol and dichloromethane
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d70e2b1e6b448e88ed08ee91b3da1a2
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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