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

HRID 1907577Notes

Reaction equation

HRID 1907577 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]([CH3:14])[CH:8]=2)[N:3]=1.Cl[C:16]([O:18][CH2:19][CH3:20])=[O:17].N1C=CC=CC=1>ClCCl>[CH3:13][O:12][C:11]1[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][CH3:20])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([CH3:14])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 69241680HCID 69241680, compound

Product 1

HCID 69243736ethyl N-(3-methoxy-6-methylquinoxalin-2-yl)carbamateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-3-methoxy-6-methylquinoxaline (1.15 g, 6.08 mmol) and ethyl chloroformate (1.32 g, 12.2 mmol) were dissolved in dichloromethane (30 ml) at room temperature and thereto pyridine (0.96 g, 12.2 mmol) was added. The resulting mixture was stirred at room temperature for 24 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 1.59 g of the titled compound (yield, 100%).

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-74eb5fa0b316402f93bb7211f5948f3b
Source dataset
uspto-grants-2013_12
Patent number
US08598173B2

Reaction notes

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