Dimethylformamide → 8-(2,6-Dichloro-3-nitrobenzyloxy)-2-methylquinoline

HRID 1604515Notes

Reaction equation

HRID 1604515 reaction equation
[H-].[Na+].CN(C)C=O.[OH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2.[Cl:20][C:21]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25]([Cl:32])[C:22]=1[CH2:23]Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:20][C:21]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[C:25]([Cl:32])[C:22]=1[CH2:23][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[CH:14]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 132242-Methyl-8-hydroxyquinolineHCID 24758Sodium hydrideHCID 110755881,3-Dichloro-2-(chloromethyl)-4-nitrobenzene

Product 1

HCID 104989148-(2,6-Dichloro-3-nitrobenzyloxy)-2-methylquinolineYield 89.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

To a mixture of sodium hydride (40% in oil, 2.64 g) and N,N-dimethylformamide (100 ml) was added 8-hydroxy-2-methylquinoline (10 g) in an ice-water bath. The mixture was stirred for 30 minutes at the same temperature and then 2,6-dichloro-3-nitrobenzyl chloride (15.1 g) and tetrabutylammonium iodide (100 mg) were added therein. The reaction mixture was stirred at ambient temperature for 1 hour. To this mixture was added water (100 ml) in an ice-water bath. The precipitates were collected by vacuum filtration and washed with water (60 ml) to give 8-(2,6-dichloro-3-nitrobenzyloxy)-2-methylquinoline (20.36 g) as a powder.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  2. filtrationThe precipitates were collected by vacuum filtration
  3. washwashed with water (60 ml)

Sources & evidence

ORD record
ord-6935eb372d114525b8f2f3979def1154
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

Loading…