Stannous chloride dihydrate → HCID 10844262, compound

HRID 2270930Notes

Reaction equation

HRID 2270930 reaction equation
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[C:16]([Cl:17])=[N:15][C:14]2[C:9](=[CH:10][C:11]([Cl:22])=[C:12]([Cl:21])[C:13]=2[N+:18]([O-])=O)[N:8]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:18][C:13]1[C:12]([Cl:21])=[C:11]([Cl:22])[CH:10]=[C:9]2[C:14]=1[N:15]=[C:16]([Cl:17])[C:7]([Cl:6])=[N:8]2

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 107575382,3,6,7-Tetrachloro-5-nitro-quinoxaline

Product 1

HCID 10844262HCID 10844262, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tin(II) chloride dihydrate (346.3 g, 1.54 mol) was added to a solution of 2,3,6,7-tetrachloro-5-nitroquinoxaline (96.2 g, 0.31 mol) in ethyl acetate (1.8 liters). The mixture was heated under reflux for 4 hours, cooled and poured cautiously into an excess of aqueous saturated sodium bicarbonate solution. The mixture was filtered through CELITE (trade mark) filter aid washing well with ethyl acetate. The filter cake was macerated with further ethyl acetate and the solid material filtered off. The combined ethyl acetate phases were dried (MgSO4) and concentrated under reduced pressure to give 5-amino-2,3,6,7-tetrachloroquinoxaline (73.4 g, 84%) as a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. filtrationThe mixture was filtered through CELITE (trade mark)
  5. filtrationfilter aid
  6. washwashing well with ethyl acetate
  7. filtrationthe solid material filtered off
  8. dry with materialThe combined ethyl acetate phases were dried (MgSO4)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e40f8a75710e4158a8c664bbc752055f
Source dataset
uspto-grants-2001_12
Patent number
US06333326B1

Reaction notes

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