Water → HCID 1794248, compound

HRID 720318Notes

Reaction equation

HRID 720318 reaction equation
[Se](=O)=O.[OH2:4].[CH3:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:20][CH3:21])=[C:11]([O:18][CH3:19])[C:12]=2[O:16][CH3:17])[N:7]=1>O1CCOCC1>[CH3:17][O:16][C:12]1[C:11]([O:18][CH3:19])=[C:10]([O:20][CH3:21])[CH:9]=[C:8]2[C:13]=1[CH:14]=[CH:15][C:6]([CH:5]=[O:4])=[N:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 140009745,6,7-Trimethoxy-2-methylquinoline

Product 1

HCID 1794248HCID 1794248, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
45 °C

Procedure

Selenium dioxide (980 mg) was suspended in a mixed solvent of dioxane (12 mL) and water (0.5 mL), and the suspension was heated to 45° C. A solution of 2-methyl-5,6,7-trimethoxyquinoline (1.97 g) in dioxane (3 mL) was slowly added dropwise thereto, and the mixture was heated to 105° C. and stirred for 1.5 hours. After allowing the reaction mixture to room temperature, selenium dioxide was filtered, and the filtrate was concentrated and purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound.

Workup

  1. temperaturethe mixture was heated to 105° C.
  2. customto room temperature
  3. filtrationselenium dioxide was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-14a4b641bcb54b3ab4793b80b97a6295
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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