Methanesulfonic Acid → 9-Ethyl-1,4,7,8,9,10-hexahydro-6-nitro-pyrido-[3,4-f]quinoxaline-2,3-dione Methanesulfonate

HRID 48226Notes

Reaction equation

HRID 48226 reaction equation
[CH2:1]([N:3]1[CH2:16][CH2:15][C:14]2[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:11]3[NH:10][C:9](=[O:20])[C:8](=[O:21])[NH:7][C:6]=3[C:5]=2[CH2:4]1)[CH3:2].[CH3:22][S:23]([OH:26])(=[O:25])=[O:24]>CN(C)C=O>[CH3:22][S:23]([OH:26])(=[O:25])=[O:24].[CH2:1]([N:3]1[CH2:16][CH2:15][C:14]2[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:11]3[NH:10][C:9](=[O:20])[C:8](=[O:21])[NH:7][C:6]=3[C:5]=2[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 10266209(9S)-9-ethyl-3-hydroxy-6-nitro-7,8,9,10-tetrahydropyrido[3,4-f]quinoxalin-9-ium-2-olate

Product 1

HCID 227424649-Ethyl-1,4,7,8,9,10-hexahydro-6-nitro-pyrido-[3,4-f]quinoxaline-2,3-dione MethanesulfonateYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The product from Example 74 was suspended in 300 mL dimethylformamide and 1 mL of 3 N methanesulfonic acid added. The suspension was warmed to 100° C. The colour changed from orange to yellow and all of the solid dissolved. Solvent was evaporated in vacuo, the yellow residue washed with acetone and then dried under vacuum over P2O5 to give the title compound (0.73 g, 92% yield) mp=302-304° C.

Workup

  1. dissolutiondissolved
  2. customSolvent was evaporated in vacuo
  3. washthe yellow residue washed with acetone
  4. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-da20f6b9c3c44a1780128c8672b4caa0
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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