Dimethylformamide → HCID 22113261, compound

HRID 726298Notes

Reaction equation

HRID 726298 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[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:22]=1[CH2:23]Br>O>[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[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

6

Reactant 4

HCID 6228DimethylformamideHCID 132242-Methyl-8-hydroxyquinolineHCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzene

Product 1

HCID 22113261HCID 22113261, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of sodium hydride (40% in oil, 24 mg) and N,N-dimethylformamide (1 ml) was added 8-hydroxy-2-methylquinoline (80 mg) in an ice-water bath. The mixture was stirred for 30 minutes at the same temperature and then 2,6-dichlorobenzyl bromide (120 mg) was added therein. The reaction mixture was stirred at ambient temperature for 1 hour. To this mixture was added water (0.5 ml) in an ice-water bath. The precipitates were corrected by vacuum filtration and washed with water (3 ml) to give 8-(2,6-dichlorobenzyloxy)-2-methylquinoline (117 mg) as a white powder.

Workup

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

Sources & evidence

ORD record
ord-f732c00dffde4544b3963299238b8138
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

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