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

HRID 1878119Notes

Reaction equation

HRID 1878119 reaction equation
[NH2:1][C:2]1[C:3]([O:13][CH3:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([Cl:12])=[CH:7][CH:6]=2.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].N1C=CC=CC=1>ClCCl>[Cl:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[C:3]([O:13][CH3:14])[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][CH3:20])=[N:11]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 66918104HCID 66918104, compound

Product 1

HCID 66918182Ethyl N-(6-chloro-2-methoxyquinoxalin-3-yl)carbamateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-6-chloro-2-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 803 mg of the titled compound (yield, 95%).

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-bf228cb3e8ec45c18a1a8a8122511408
Source dataset
uspto-grants-2012_11
Patent number
US08314100B2

Reaction notes

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