HCID 178507818, compound → HCID 178507817, compound

HRID 1031099Notes

Reaction equation

HRID 1031099 reaction equation
[NH2:1][C:2]1[C:3]([N+:15]([O-])=O)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([OH:13])[C:6]([OH:14])=[N:5]2>CN(C)C=O.C(N(CC)CC)C.[Pd]>[NH2:15][C:3]1[C:2]([NH2:1])=[C:11]([Cl:12])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([OH:14])[C:7]([OH:13])=[N:8]2

Participants

5

Reactant 1

HCID 178507818HCID 178507818, compound

Product 1

HCID 178507817HCID 178507817, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3 g (11,9 mmol) 6-amino-7-chloro-5-nitro-2,3-dihydroxyquinoxaline in a mixture of 80 ml dimethylformamide and 7,5 ml triethylamine was hydrogenated at atm. pressure using 5% Pd-C (0,5 g) as a catalyst. The reaction mixture was filtered and evaporated in vacuo. The residue was stirred with 100 ml water, added 4N hydrochloric acid to pH 5-6, and the precipitate was filtered off to give 2,1 g of a crude product. Recrystallization (dimethylformamide-methanol) gave 1,95 g (74%) 5,6-diamino-7-chloro-2,3-dihydroxyquinoxaline, m.p. >300° C. NMR (DMSO-d6): 11.6 (1H, broad s), 11.0 (1H, broad m), 6.47 (1H,s), 5.1 (2H, broad s), 4.6 (2H, broad s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. additionadded 4N hydrochloric acid to pH 5-6
  4. filtrationthe precipitate was filtered off
  5. customto give 2,1 g of a crude product
  6. customRecrystallization (dimethylformamide-methanol)

Sources & evidence

ORD record
ord-c408f810d37540cbb4a8e742a0d5b543
Source dataset
uspto-grants-1992_04
Patent number
US05109001

Reaction notes

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