Pyridine → ethyl N-(6-chloro-3-methoxyquinoxalin-2-yl)carbamate

HRID 1878208Notes

Reaction equation

HRID 1878208 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:14])[CH:8]=2)[N:3]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].N1C=CC=CC=1>ClCCl>[Cl:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][CH3:20])[C:11]([O:12][CH3:13])=[N:10]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 69243355HCID 69243355, compound

Product 1

HCID 69241674ethyl N-(6-chloro-3-methoxyquinoxalin-2-yl)carbamateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-6-chloro-3-methoxyquinoxaline (629 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 811 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-922c2733855e4786a7d90758085f2317
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

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