Pyridine → Ethyl N-(2,6-dimethoxyquinoxalin-3-yl)carbamate

HRID 1878162Notes

Reaction equation

HRID 1878162 reaction equation
[NH2:1][C:2]1[C:3]([O:14][CH3:15])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].N1C=CC=CC=1>ClCCl>[CH3:15][O:14][C:3]1[C:2]([NH:1][C:17](=[O:18])[O:19][CH2:20][CH3:21])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 66918098HCID 66918098, compound

Product 1

HCID 66918080Ethyl N-(2,6-dimethoxyquinoxalin-3-yl)carbamateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-2,6-dimethoxyquinoxaline (616 mg, 3.00 mmol) and ethyl chloroformate (391 mg, 3.60 mmol) were dissolved in dichloromethane (50 ml) at room temperature and thereto pyridine (285 mg, 3.60 mmol) was added. The resulting mixture was stirred at room temperature for 10 hours and concentrated under the reduced pressure to remove the solvent, and purified by SiO2 column chromatography. Extraction of the residue with a n-hexane:ethyl acetate (3:1) mixture and concentration gave 799 mg of the titled compound (yield, 96%).

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove the solvent
  3. custompurified by SiO2 column chromatography
  4. extractionExtraction of the residue
  5. concentrationwith a n-hexane:ethyl acetate (3:1) mixture and concentration

Sources & evidence

ORD record
ord-ce193774cbce4b8b87ceea41559392aa
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

Loading…