2-Methyl-5-nitroquinoxaline → HCID 12666713, compound

HRID 1883185Notes

Reaction equation

HRID 1883185 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-])=O)[N:3]=1>CO.[Cl-].[Cl-].[Cl-].[Ti+3]>[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH2:12])[N:3]=1

Participants

4

Reactant 1

HCID 235103262-Methyl-5-nitroquinoxaline

Product 1

HCID 12666713HCID 12666713, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-5-nitroquinoxaline (3.67 g) in MeOH (350 mL) was added dropwise a 20% aqueous titanium trichloride (92.9 g) at room temperature. After the addition, the mixture was further stirred for one hour, and concentrated under reduced pressure. The resultant was neutralized by addition of aqueous sodium carbonate solution, and the mixture was extracted four times with ethyl acetate (150 mL). The organic layers were combined, and dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give 2-methyl-5-aminoquinoxaline (2.44 g,79%) as orange crystals.

Workup

  1. additionAfter the addition
  2. concentrationconcentrated under reduced pressure
  3. additionThe resultant was neutralized by addition of aqueous sodium carbonate solution
  4. extractionthe mixture was extracted four times with ethyl acetate (150 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-982551e6510242eba2cf6e33f0d12a5a
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

Loading…