Potassium Carbonate → 2-Cyano-6-benzyloxymethyl quinoline

HRID 552038

Reaction equation

HRID 552038 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8](O)[CH:9]=2)[N:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:9]=2)[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl etherHCID 144295346-Hydroxyquinoline-2-carbonitrile

Product 1

HCID 668385032-Cyano-6-benzyloxymethyl quinoline

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-cyano-6-hydroxyquinoline (100 mg) in 10 mL of acetone was added potassium carbonate (122 mg). After stirring at RT for three minutes, the solution was put on ice. Benzyl chloromethyl ether (122 μL) was added through a needle and the resultant solution was stirred on ice for 2 hours. The solvent was then removed under vacuum and the residue was purified by flash chromatography with dichloromethane. 157 mg was obtained.

Workup

  1. customThe solvent was then removed under vacuum
  2. customthe residue was purified by flash chromatography with dichloromethane
  3. custom157 mg was obtained

Sources & evidence

ORD record
ord-5390042237a04690abb0a489ead1d619
Source dataset
uspto-grants-2011_05
Patent number
US07951550B2

Linked notes

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