Dimethylformamide → [8-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetonitrile

HRID 2266469Notes

Reaction equation

HRID 2266469 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[C:7]([CH3:21])[C:6]=2[C:5]([OH:22])=[CH:4][CH:3]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]#[N:37]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:35][C:36]#[N:37])=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:7]2[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 1363358958-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol

Product 1

HCID 68783934[8-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-ol (0.80 g), N,N-dimethylformamide (10 mL), potassium carbonate (1.0 g) and bromoacetonitrile (0.25 mL) was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate and this mixture was washed with water and saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound as a light brown solid, 0.90 g.

Workup

  1. washthis mixture was washed with water and saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-04ab033375054736a28732fb37434444
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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