N-Methylbenzylamine → N-(2,3-Dioxo-7-nitro-1,2,3,4-tetrahydroquinoxalin-5-ylmethyl)-N-methylbenzylamine hydrobromide

HRID 1422234Notes

Reaction equation

HRID 1422234 reaction equation
[Br:1][CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:18]C)[C:7]([O:16]C)=[N:8]2.[CH2:20]([NH:27][CH3:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C>[BrH:1].[O:16]=[C:7]1[C:6](=[O:18])[NH:5][C:4]2[C:9](=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:3]=2[CH2:2][N:27]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:28])[NH:8]1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 232979835-Bromomethyl-7-nitro-2,3-dimethoxyquinoxaline

Product 1

HCID 18706367N-(2,3-Dioxo-7-nitro-1,2,3,4-tetrahydroquinoxalin-5-ylmethyl)-N-methylbenzylamine hydrobromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

200 mg of 5-bromomethyl-2,3-dimethoxy-7-nitro-quinoxaline and 0.016 ml (2.2 equiv.) of N-benzyl-methylamine are dissolved in 10 ml of acetonitrile, and the solution is stirred at reflux for 20 hours. The mixture is concentrated by evaporation, and the residue is dissolved in ethyl acetate and washed in aqueous 5% sodium carbonate solution and brine. The organic phase is dried over magnesium sulfate and the solvent is concentrated by evaporation.

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationThe mixture is concentrated by evaporation
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed in aqueous 5% sodium carbonate solution and brine
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationthe solvent is concentrated by evaporation

Sources & evidence

ORD record
ord-08dcbbed354d4568b88df4ac33881d14
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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