6-Hydroxyquinoline → HCID 23130717, compound

HRID 2080262Notes

Reaction equation

HRID 2080262 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Cl)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)([O-])C.[K+]>CS(C)=O>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][O:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:1]=[CH:2][CH:3]=[CH:4]3)=[CH:24][CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 113746-HydroxyquinolineHCID 700424-Benzyloxybenzyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 23130717HCID 23130717, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of quinoline-6-ol (37 mg, 0.25 mmol), 1-benzyloxy-4-chloromethyl-benzene (70 mg, 0.30 mmol) in dimethylsulfoxide (2.5 mL) was added potassium tert-butoxide (43 mg, 0.38 mmol) under nitrogen atmosphere, and the solution was stirred for 13 hours at room temperature. This reaction solution was purified by thin layer silica gel chromatography (hexane:ethyl acetate=1:1), and the title compound (74 mg, 0.217 mmol, 86%) was obtained as a pale yellow solid.

Workup

  1. customThis reaction solution was purified by thin layer silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2f5024c058ce4235851731610b79e25e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…