2-Nitro-N-quinoxalin-5-yl-benzenesulfonamide → 2-Amino-N-quinoxalin-5-yl-benzenesulfonamide

HRID 513590Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[N:16]=[CH:17][CH:18]=[N:19]2)(=[O:12])=[O:11])([O-])=O>CC(O)=O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[N:16]=[CH:17][CH:18]=[N:19]2)(=[O:12])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Iron powder (455 mg, 8.14 mmol) was added to a solution of 2-nitro-N-quinoxalin-5-yl-benzenesulfonamide (Intermediate 243) (673 mg, 2.08 mmol) in AcOH (15 ml) and the mixture was heated at 80° C. for 2 h. After cooling, the mixture was concentrated in vacuo. The residue was diluted with EtOAc and the mixture was filtered through celite. The filtrate was washed with sat. NaHCO3 solution, dried (Na2SO4) and concentrated in vacuo to give the title compound (440 mg, 72%) which was used in the next step without further purification.

Workup

temperatureAfter cooling
concentrationthe mixture was concentrated in vacuo
additionThe residue was diluted with EtOAc
filtrationthe mixture was filtered through celite
washThe filtrate was washed with sat. NaHCO3 solution
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e394ed13e97147fd8287ce9f54735644
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102688B2

Reaction notes

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