Reaction #76504

ord-da20f6b9c3c44a1780128c8672b4caa0

Reaction equation

CCN1CCc2c([N+](=O)[O-])cc3[nH]c(=O)c(=O)[nH]c3c2C1
product
CCN1CCc2c([N+](=O)[O-])cc3[nH]c(=O)c(=O)[nH]c3c2C1
9-Ethyl-1,4,7,8,9,10-hexahydro-6-nitro-pyrido[3,4-f]quinoxaline-2,3-dione
CS(=O)(=O)O
methanesulfonic acid
→
CCN1CCc2c([N+](=O)[O-])cc3[nH]c(=O)c(=O)[nH]c3c2C1.CS(=O)(=O)O
title compound
Yield 92.0%
CCN1CCc2c([N+](=O)[O-])cc3[nH]c(=O)c(=O)[nH]c3c2C1.CS(=O)(=O)O
9-Ethyl-1,4,7,8,9,10-hexahydro-6-nitro-pyrido-[3,4-f]quinoxaline-2,3-dione methanesulfonate
Yield 92.0%

Reactants

CCN1CCc2c([N+](=O)[O-])cc3[nH]c(=O)c(=O)[nH]c3c2C1
product
CCN1CCc2c([N+](=O)[O-])cc3[nH]c(=O)c(=O)[nH]c3c2C1
9-Ethyl-1,4,7,8,9,10-hexahydro-6-nitro-pyrido[3,4-f]quinoxaline-2,3-dione
CS(=O)(=O)O
methanesulfonic acid

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Temperature
100°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.DISSOLUTIONdissolved
  2. 2
    OtherSolvent was evaporated in vacuo
  3. 3
    Washthe yellow residue washed with acetone
  4. 4
    Dryingdried under vacuum over P2O5

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06703391B2uspto-grants-2004_03