Potassium Carbonate → {2-[3-(Quinolin-2-ylmethoxy)phenoxymethyl]-6-methylphenoxy}acetonitrile

HRID 892166Notes

Reaction equation

HRID 892166 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.Br[CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[O:24][CH2:25][C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][CH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:23]=1[O:24][CH2:25][C:26]#[N:27]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-HCID 222414892-Cyanomethoxy-3-methylbenzyl bromide

Product 1

HCID 22241372{2-[3-(Quinolin-2-ylmethoxy)phenoxymethyl]-6-methylphenoxy}acetonitrile

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

3-(Quinolin-2-ylmethoxy)-phenol (1.3 g, 5.4 mmol, example 3), (2-bromomethyl-6-methyl-phenoxy)-acetonitrile (1.56 g, 6.5 mmol, example 24), tetrabutylammonium iodide (99 mg, 0.27 mmol) and potassium carbonate (0.45 g, 3.3 mmol) are refluxed in acetone (20 mL) for 16 h. The reaction is filtered, washed with dichloromethane, concentrated and purified by column chromatography (silica, 1% ether in dichloromethane) to provide the title compound. MS (ESI) 411 (M+H)+.

Workup

  1. filtrationThe reaction is filtered
  2. washwashed with dichloromethane
  3. concentrationconcentrated
  4. custompurified by column chromatography (silica, 1% ether in dichloromethane)

Sources & evidence

ORD record
ord-c8707e5628f84cdfaff56bb4111b810f
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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