2-Nitropropane → 2,3-Dimethoxyquinoxaline-5-carbaldehyde

HRID 1422251Notes

Reaction equation

HRID 1422251 reaction equation
[N+](C(C)C)([O-])=[O:2].[Na].[CH3:8][O:9][C:10]1[C:19]([O:20][CH3:21])=[N:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[CH2:22]Br)[N:11]=1>CO>[CH3:8][O:9][C:10]1[C:19]([O:20][CH3:21])=[N:18][C:17]2[C:16]([CH:22]=[O:2])=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 5360545SodiumHCID 159417295-Bromomethyl-2,3-dimethoxy-quinoxaline

Product 1

HCID 159417302,3-Dimethoxyquinoxaline-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

17 ml (188 mmol) of 2-nitropropane are added to a solution of 3.7 g (163 mmol) of sodium in 700 ml of methanol. After 5 minutes' stirring, 35.5 g (125.4 mmol) of solid 2,3-dimethoxy-5-bromomethyl-quinoxaline are added. The mixture is heated at reflux for 1 hour, a homogeneous solution being formed. After cooling, the solution is concentrated under reduced pressure. The residue is taken up in ethyl acetate and 1 N HCl, the phases are separated and the organic phase is washed with water and brine, dried over sodium sulfate and concentrated. The title compound is isolated in the form of white crystals by crystallization from ethyl acetate.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 1 hour
  3. customa homogeneous solution being formed
  4. temperatureAfter cooling
  5. concentrationthe solution is concentrated under reduced pressure
  6. custom1 N HCl, the phases are separated
  7. washthe organic phase is washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2280810750bd479098b9d486ca539fb0
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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