Stannous chloride dihydrate → HCID 54395338, compound

HRID 343810Notes

Reaction equation

HRID 343810 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:18])=[C:7]([CH2:16][CH3:17])[C:8]=2[N+:13]([O-])=O)[N:3]=1.[Cl:19][C:20]1[C:29]([Cl:30])=[N:28][C:27]2[C:22](=[CH:23][C:24]([CH2:35][CH3:36])=[C:25]([Cl:34])[C:26]=2[N+:31]([O-])=O)[N:21]=1.O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[NH2:13][C:8]1[C:7]([CH2:16][CH3:17])=[C:6]([Cl:18])[CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([Cl:12])[C:2]([Cl:1])=[N:3]2.[NH2:31][C:26]1[C:25]([Cl:34])=[C:24]([CH2:35][CH3:36])[CH:23]=[C:22]2[C:27]=1[N:28]=[C:29]([Cl:30])[C:20]([Cl:19])=[N:21]2

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 53641830HCID 53641830, compoundHCID 54353091HCID 54353091, compound

Product 2

HCID 54395338HCID 54395338, compoundYield 91%HCID 54482221HCID 54482221, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2,3,7-trichloro-6-ethyl-5-nitroquinoxaline and 2,3,6-trichloro-7-ethyl-5-nitroquinoxaline (200 mg, 0.652 mmol), tin (II) chloride dihydrate (1.03 g, 4.57 mmol) and ethyl acetate (6.5 ml) was heated under reflux for 4h, cooled and diluted with ethyl acetate. The solution was washed with 10% aqueous sodium carbonate (25 ml). The aqueous layer was extracted with ethyl acetate (2×25 ml), and the combined organic solutions were washed with 10% aqueous sodium carbonate (2×25 ml), saturated aqueous sodium chloride (25 ml), dried (MgSO4) and concentrated under reduced pressure to give 5-amino-2,3,7-trichloro-6-ethylquinoxaline and 5-amino-2,3,6-trichloro-7-ethylquinoxaline as an orange solid (174 mg, 91%), ratio 1:1.

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. washThe solution was washed with 10% aqueous sodium carbonate (25 ml)
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×25 ml)
  5. washthe combined organic solutions were washed with 10% aqueous sodium carbonate (2×25 ml), saturated aqueous sodium chloride (25 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40a2716424af433db0dd7ec30ab99c36
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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