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

HRID 1907637Notes

Reaction equation

HRID 1907637 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-eb907cd78a474d8590f8108bb556cf08
Source dataset
uspto-grants-2013_12
Patent number
US08598173B2

Reaction notes

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