Pyridine → Ethyl N-(2-methoxy-6,7-dimethylquinoxalin-3-yl)carbamate

HRID 1878291Notes

Reaction equation

HRID 1878291 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]2[C:4](=[CH:5][C:6]([CH3:15])=[C:7]([CH3:14])[CH:8]=2)[N:3]=1.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].N1C=CC=CC=1>ClCCl>[CH3:13][O:12][C:11]1[C:2]([NH:1][C:17](=[O:18])[O:19][CH2:20][CH3:21])=[N:3][C:4]2[C:9](=[CH:8][C:7]([CH3:14])=[C:6]([CH3:15])[CH:5]=2)[N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 69243755HCID 69243755, compound

Product 1

HCID 69244399Ethyl N-(2-methoxy-6,7-dimethylquinoxalin-3-yl)carbamateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-3-methoxy-6,7-dimethylquinoxaline (2.34 g, 11.5 mmol) and ethyl chloroformate (2.50 g, 23.0 mmol) were dissolved in dichloromethane (50 ml) at room temperature and thereto pyridine (1.82 g, 23.0 mmol) was added. The mixture was stirred at room temperature for 12 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 2.65 g of the titled compound (yield, 84%).

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-d32805d104cd4491b36b366607347486
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

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