hydroxylamine-O-sulfonic acid → 1-Amino-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione

HRID 439467Notes

Reaction equation

HRID 439467 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[NH:4][C:5](=[O:14])[C:6](=[O:13])[NH:7]2.[NH2:15]OS(O)(=O)=O>[OH-].[K+].O>[NH2:15][N:7]1[C:8]2[C:3](=[C:2]([Cl:1])[CH:11]=[C:10]([Cl:12])[CH:9]=2)[NH:4][C:5](=[O:14])[C:6]1=[O:13]

Participants

5

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 6502605,7-Dichloro-1,4-dihydroquinoxaline-2,3-dione

Product 1

HCID 199586181-Amino-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedioneYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

The procedure of Wallace, R. G., Org. Prep. Proc. Int. 14:269 (1982) was adapted. 5,7-Dichloro-1,4-dihydroquinoxaline-2,3-dione (52 mg, 0.225 mmole) was dissolved in 3N KOH (1 mL) at 60° C. for 0.5 h, and NH2OSO3H (30 mg, 0.265 mmole, Aldrich) in distilled water (0.5 mL) was dropwise added into above solution with stirring at 60° C. Some precipitate came out after 15 mins. The mixture was stirred at room temperature overnight. The white precipitate was collected by filtration, washed with cold distilled water (0.5 mL) and dried on rotavapor at 60° C. for 2 h affording crude 1-amino-5,7-dichloro-1,4-dihydro-2,3-quinoxalinedione (38 mg, 69%), which included a little of the isomer (4-amino-5,7-dichloro-2,3-quinoxalinedione) by 1H NMR (it is not known which isomer is present in a greater amount).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationThe white precipitate was collected by filtration
  3. washwashed
  4. distillationwith cold distilled water (0.5 mL)
  5. customdried on rotavapor at 60° C. for 2 h

Sources & evidence

ORD record
ord-d437b03e594443c5b8cac63d165f4a06
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

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