Ammonium Chloride → HCID 13750559, compound

HRID 1445476Notes

Reaction equation

HRID 1445476 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:13]([O-])=O)[CH:9]=2)[N:4]=1.[Cl-].[NH4+]>[Fe].CO>[CH3:1][O:2][C:3]1[CH:12]=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:13])[CH:9]=2)[N:4]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 150258562-Methoxy-6-nitroquinoxaline

Product 1

HCID 13750559HCID 13750559, compoundYield 124.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

Into 20 ml of methanol was dissolved 726 mg of 2-methoxy-6-nitroquinoxaline, and then 1.0 g of iron powder and a saturated ammonium chloride aqueous solution were added thereto, followed by heating under refluxing overnight. Insoluble matter was separated by filtration using celite and then the solvent was removed by evaporation. A sodium bicarbonate aqueous solution was added to the residue, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by evaporation and the resulting residue was purified by silica gel column chromatography to obtain 770 mg of the title compound from chloroform-methanol (100:1, v/v).

Workup

  1. temperatureby heating
  2. temperatureunder refluxing overnight
  3. customInsoluble matter was separated by filtration
  4. customthe solvent was removed by evaporation
  5. additionA sodium bicarbonate aqueous solution was added to the residue
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed by evaporation
  9. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f6632d67e2df49c9be604e13f4098eb3
Source dataset
uspto-grants-2010_02
Patent number
US07666873B2

Reaction notes

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