1-(3,3-Dimethoxypropyl)-7-methoxy-3,4-dihydroquinoxalin-2(1H)one → 1-(3,3-Dimethoxypropyl)-7-methoxyquinoxalin-2(1H)-one

HRID 1847082Notes

Reaction equation

HRID 1847082 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][CH2:8][C:7]1=[O:18]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:20][O:19][CH:3]([O:2][CH3:1])[CH2:4][CH2:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][C:7]1=[O:18]

Participants

4

Reactant 1

HCID 867250051-(3,3-Dimethoxypropyl)-7-methoxy-3,4-dihydroquinoxalin-2(1H)one

Product 1

HCID 867249271-(3,3-Dimethoxypropyl)-7-methoxyquinoxalin-2(1H)-oneYield 72%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (10 ml) was dissolved 1-(3,3-dimethoxypropyl)-7-methoxy-3,4-dihydroquinoxalin-2(1H)one (201 mg, 0.717 mmol) under a nitrogen gas atmosphere, manganese dioxide (733 mg, 7.17 mmol) was added thereto at room temperature and the mixture was stirred at the same temperature for 17 hours. The insoluble material was removed by filtration using celite, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 143 mg (72%) of the title compound in the form of a yellowish solid.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-56529800bdd74b0d99adaf9d91dd2be2
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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