2-Methyl-8-hydroxyquinoline → 8-(2,6-Dimethyl-3-nitrobenzyloxy)-2-methylquinoline

HRID 1699171Notes

Reaction equation

HRID 1699171 reaction equation
CS([O:5][CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]=1[CH3:17])(=O)=O.CC1C([N+]([O-])=O)=CC=C(C)C=1CCl.[H-].[Na+].O[C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:43]=1[N:42]=[C:41]([CH3:44])[CH:40]=[CH:39]2>CN(C)C=O.O>[CH3:17][C:8]1[C:9]([N+:14]([O-:16])=[O:15])=[CH:10][CH:11]=[C:12]([CH3:13])[C:7]=1[CH2:6][O:5][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:43]=1[N:42]=[C:41]([CH3:44])[CH:40]=[CH:39]2

Participants

7

Reactant 4

HCID 132242-Methyl-8-hydroxyquinolineHCID 24758Sodium hydrideHCID 183217552,6-Dimethyl-3-nitrobenzyl chlorideHCID 183219512,6-Dimethyl-3-nitrobenzyl methanesulfonate

Product 1

HCID 183218528-(2,6-Dimethyl-3-nitrobenzyloxy)-2-methylquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,6-dimethyl-3-nitrobenzyl methanesulfonate and 2,6-dimethyl-3-nitrobenzyl chloride obtained above in N,N-dimethylformamide (13 ml) was added sodium hydride (60% in oil, 335 mg) under ice-bath cooling, and the mixture was stirred for 15 minutes. To the mixture was added 8-hydroxy-2-methylquinoline (1.27 g), and the mixture was stirred for 1 hour at ambient temperature. Water was added thereto, and the resulting precipitate was collected by filtration to give 8-(2,6-dimethyl-3-nitrobenzyloxy)-2-methylquinoline (2.53 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hour at ambient temperature
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cf8f39a6273143a18d87e606720cf44a
Source dataset
uspto-grants-2002_02
Patent number
US06344462B1

Reaction notes

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