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

HRID 1953778Notes

Reaction equation

HRID 1953778 reaction equation
[N+](C(C)C)([O-])=[O:2].[Na].Br[CH2:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[N:12]=[C:13]([O:22][CH3:23])[C:14]([O:20][CH3:21])=[N:15]2>CO>[CH3:21][O:20][C:14]1[C:13]([O:22][CH3:23])=[N:12][C:11]2[C:10]([CH:9]=[O:2])=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=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 stirring for 5 minutes, 35.5 g (125.4 mmol) of solid 5-bromomethyl-2,3-dimethoxyquinoxaline are added. The mixture is heated to reflux for 1 hour, a homogeneous solution resulting. After cooling, the solution is concentrated under reduced pressure. The residue is taken up in ethyl acetate and 1N hydrochloric acid, 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. M.p. 137-140°; TLC (ethyl acetate/hexane 1:3): Rf =0.45.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1 hour
  3. customa homogeneous solution resulting
  4. temperatureAfter cooling
  5. concentrationthe solution is concentrated under reduced pressure
  6. custom1N hydrochloric acid, 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-274be7a2e58e48bc858947406e7da89d
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

Loading…