Sulfuric Acid → 1,4,7,8,9,10-Hexahydro-9-methyl-6-nitro-pyrido-[3.4-f]quinoxaline-2,3-dione Methansulfonate

HRID 48227Notes

Reaction equation

HRID 48227 reaction equation
Cl.[CH3:2][N:3]1[CH2:16][CH2:15][C:14]2[CH:13]=[CH:12][C:11]3[NH:10][C:9](=[O:17])[C:8](=[O:18])[NH:7][C:6]=3[C:5]=2[CH2:4]1.[N+:19]([O-])([O-:21])=[O:20].[K+].[OH-].[NH4+].[S:26](=[O:30])(=O)([OH:28])[OH:27]>>[CH3:2][S:26]([OH:28])(=[O:30])=[O:27].[CH3:2][N:3]1[CH2:16][CH2:15][C:14]2[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:11]3[NH:10][C:9](=[O:17])[C:8](=[O:18])[NH:7][C:6]=3[C:5]=2[CH2:4]1

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 227424951,4,7,8,9,10-Hexahydro-9-methyl-pyrido-[3,4-f]quinoxaline-2,3-dione Monohydrochloride

Product 1

HCID 217157361,4,7,8,9,10-Hexahydro-9-methyl-6-nitro-pyrido-[3.4-f]quinoxaline-2,3-dione MethansulfonateYield 100%

Procedure

A solution of the product from Example 77 (0.64 g, 2.77 mmol) in 20 mL concentrated sulfuric acid was treated with potassium nitrate (0.29 g, 2.87 mmol) in 2 mL concentrated sulfuric acid. After stirring overnight at room temperature the reaction mixture was poured onto ice, cooled in a dry ice bath, and then basified with ammonium hydroxide to pH 8.9. The orange/yellow solid was collected by filtration and washed consecutively with water, acetone and ether and dried to give the title compound (0.78 g, 100% yield).

Workup

  1. additionwas poured onto ice
  2. temperaturecooled in a dry ice bath
  3. filtrationThe orange/yellow solid was collected by filtration
  4. washwashed consecutively with water, acetone and ether
  5. customdried

Sources & evidence

ORD record
ord-5358a26098614724b2d487aa49360715
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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