Sodium Hydroxide → HCID 178432344, compound

HRID 1031114Notes

Reaction equation

HRID 1031114 reaction equation
[OH:1][C:2]1[C:3]([OH:18])=[N:4][C:5]2[C:6]([N:17]=1)=[C:7]1[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([CH3:15])[C:9]([CH3:16])=[N:8]1.[N+:19]([O-])([O-:21])=[O:20].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[OH:1][C:2]1[C:3]([OH:18])=[N:4][C:5]2[C:6]([N:17]=1)=[C:7]1[C:12](=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=2)[N:11]=[C:10]([CH3:15])[C:9]([CH3:16])=[N:8]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 178432086HCID 178432086, compound

Product 1

HCID 178432344HCID 178432344, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 0,45 g (1,9 mmol) 2,3-dihydroxy-8,9-dimethylpyrazino(2,3-f)quinoxaline in 30 ml concentrated sulfuric acid was added at 0° C. 384 mg (3,8 mmol) potassium nitrate. Stirring was continued at 0° C. for 30 min. and at 25° C. for 24 h. The reaction mixture was poured into 150 ml icewater. The solution was added 10N sodium hydroxide to pH 7, and then extracted with ethyl acetate (5×100 ml). The combined and dried ethyl acetate phases were evaporated to give 0,18 g (33%) 2,3-dihydroxy-8,9-dimethyl-6-nitropyrazino(2,3-f)quinoxaline, m.p. >300° C. NMR (DMSO-d6): 8.07 (1H,s), 2.77 (3H,s), 2.73 (3H,s).

Workup

  1. additionThe reaction mixture was poured into 150 ml icewater
  2. extractionextracted with ethyl acetate (5×100 ml)
  3. customdried ethyl acetate phases were evaporated

Sources & evidence

ORD record
ord-73f7519eae8a42bfad59a17a49ab289e
Source dataset
uspto-grants-1992_04
Patent number
US05109001

Reaction notes

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