Hydrochloric Acid → HCID 178507220, compound

HRID 1165827Notes

Reaction equation

HRID 1165827 reaction equation
[OH:1][C:2]1[C:3]([OH:23])=[N:4][C:5]2[CH:6]=[C:7]([N+:20]([O-])=O)[C:8]3[C:15]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[N:11]=1.Cl>CN(C)C=O.[Ni]>[NH2:20][C:7]1[C:8]2[C:15]([S:16](=[O:18])(=[O:19])[NH2:17])=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]2[N:11]=[C:2]([OH:1])[C:3]([OH:23])=[N:4][C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178514693HCID 178514693, compound

Product 1

HCID 178507220HCID 178507220, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 0,5 g (1,49 mmol) 2,3-dihydroxy-6-nitro-7-sulphamoyl-benzo[f]quinoxaline in 5 ml dimethylformamide was hydrogenated at atm. pressure by using ca. 1 g Ra-Ni as a catalyst. The filtered reaction mixture was added 5 ml 1N hydrochloric acid, and then evaporated in vacuo. The crude product was recrystallized (dimethylformamide-water) to give 0,2 g (40%) 6-amino-2,3-dihydroxy-7-sulphamoyl-benzo[f]quinoxaline as a hydrochloride salt. MS: (m/e) 306 (M+ ; 75%). NMR (DMSO-6): 11,8 (2H, broad s), 8.7 (1H,d), 8.2 (1H,d), 7.6 (3H,m), 6.93 (1H,s), 6.1 (2H, broad s).

Workup

  1. customThe filtered reaction mixture
  2. customevaporated in vacuo
  3. customThe crude product was recrystallized (dimethylformamide-water)

Sources & evidence

ORD record
ord-fd3d246389fb4fd6b7c740bcb8fa9862
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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