Sodium Bicarbonate → HCID 53808462, compound

HRID 1458569Notes

Reaction equation

HRID 1458569 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][C:6]([CH3:17])=[C:7]([CH3:16])[C:8]=2[N+:13]([O-])=O)[N:3]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:13][C:8]1[C:7]([CH3:16])=[C:6]([CH3:17])[CH:5]=[C:4]2[C:9]=1[N:10]=[C:11]([Cl:12])[C:2]([Cl:1])=[N:3]2

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 53663187HCID 53663187, compound

Product 1

HCID 53808462HCID 53808462, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2,3-dichloro-6,7-dimethyl-5-nitroquinoxaline (from step (b), 8.33 g, 30.6 mmol) and stannous chloride dihydrate (34.54 g, 153 mmol) in ethyl acetate (300 ml) was heated at reflux for 11 hours. A further portion of stannous chloride dihydrate (13.82 g, 61.2 mmol) was added and the mixture was heated for 2 hours, cooled and diluted with ethyl acetate (500 ml). The mixture was added to saturated aqueous sodium bicarbonate (200 ml) and filtered, washing the filter cake well with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium bicarbonate (3×100 ml), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with methanol/dichloromethane) to afford 5-amino-2,3-dichloro-6,7-dimethylquinoxaline (6.15 g, 83%), as an orange solid, m.p. 178-180° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 11 hours
  3. temperaturethe mixture was heated for 2 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. washwashing the filter cake well with ethyl acetate
  7. customThe organic layer was separated
  8. washwashed with saturated aqueous sodium bicarbonate (3×100 ml)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash chromatography (gradient elution with methanol/dichloromethane)

Sources & evidence

ORD record
ord-5b2cb437616143b3a50eb59b37fe9ea9
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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