4-Iodophenol → 4-(4-Iodo-phenoxymethyl)-2-methylquinoline

HRID 719398Notes

Reaction equation

HRID 719398 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([CH3:13])[CH:4]=1.[I:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[I:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:2][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[C:5]([CH3:13])[CH:4]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 115357194-(Chloromethyl)-2-methylquinoline

Product 1

HCID 218980594-(4-Iodo-phenoxymethyl)-2-methylquinolineYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a CH3CN (200 mL) solution of 4-chloromethyl-2-methylquinoline (10.22 g, 53.3 mmol) and 4-iodophenol (11.98 g, 1.02 eq) was added K2CO3. The suspension was heated to reflux for 6 h. The mixture was then filtered through Celite® while the solution was still hot. The 4-(4-iodo-phenoxymethyl)-2-methylquinoline (20 g, 100%) was obtained as fine crystals after recrystalization in CH3CN.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 6 h
  3. filtrationThe mixture was then filtered through Celite® while the solution

Sources & evidence

ORD record
ord-807086318fd34bdab4665794adabbdc5
Source dataset
uspto-grants-2006_11
Patent number
US07132432B2

Reaction notes

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