Benzyl Bromide → HCID 59829697, compound

HRID 551116Notes

Reaction equation

HRID 551116 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O.C(OCC)C>[CH2:1]([C:4]1[C:13]([O:14][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7498Benzyl Bromide2×HCID 11430Potassium Carbonate2×HCID 36549187-Prop-2-enylquinolin-8-ol

Product 1

HCID 59829697HCID 59829697, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirring solution of 7-allylquinolin-8-ol (14.56 mmol, 1 eq.) in acetone (50 mL) in a round bottom flask equipped with a reflux condenser was added potassium carbonate (151.94 mmol, 10.44 eq.) followed by benzyl bromide (17.47 mmol, 1.2 eq.) and the resulting solution was stirred and heated to reflux for 20 h. Additional potassium carbonate (151.94 mmol, 10.44 eq.) was added followed by additional benzyl bromide (29.12 mmol, 2 eq.) and the resulting mixture was heated at reflux and stirred 2 h. The reaction mixture was then cooled to room temperature and diluted with 50 mL of diethyl ether. The resulting suspension was filtered and the filtrate concentrated to a yellow oil that was purified by column chromatography using 10% acetone/dichloromethane to give the product as a pale yellow oil (10.48 mmol, 72%). MS (ESI) m/z 276.2; HRMS: calcd for C19H17NO+H+, 276.13829; found (ESI-FTMS, [M+H]1+), 276.13828.

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 h
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux
  5. stirringstirred 2 h
  6. filtrationThe resulting suspension was filtered
  7. concentrationthe filtrate concentrated to a yellow oil that
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-194ad1fa34004480870ae71d8abe4131
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

Loading…