Pyridine → Ethyl N-(2-methoxy-6-methylquinoxalin-3-yl)carbamate

HRID 1907486Notes

Reaction equation

HRID 1907486 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]([CH3:12])=[CH:7][CH:6]=2.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].N1C=CC=CC=1>ClCCl>[CH3:14][O:13][C:3]1[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][CH3:20])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:12])[CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 66918137HCID 66918137, compound

Product 1

HCID 66917958Ethyl N-(2-methoxy-6-methylquinoxalin-3-yl)carbamateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-2-methoxy-6-methylquinoxaline (568 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 n-hexane:ethyl acetate (3:1) mixture and concentration gave 768 mg of the titled compound (yield, 98%).

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 n-hexane:ethyl acetate (3:1) mixture and concentration

Sources & evidence

ORD record
ord-53fe07a4b1bd4dc4958dc6e0c80b04ba
Source dataset
uspto-grants-2013_12
Patent number
US08598173B2

Reaction notes

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