Water → 4-(4-Methanesulfonylphenoxymethyl)-2-methylquinoline

HRID 1788362Notes

Reaction equation

HRID 1788362 reaction equation
Cl.Cl[CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[C:6]([CH3:14])[CH:5]=1.[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17].[OH-].[Na+].O>C(O)C>[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:3][C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=[C:6]([CH3:14])[CH:5]=2)=[CH:21][CH:20]=1)(=[O:17])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 1233504-(Methylsulfonyl)phenolHCID 222278114-Chloromethyl-2-methylquinoline hydrochloride

Product 1

HCID 230180214-(4-Methanesulfonylphenoxymethyl)-2-methylquinolineYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7.23 g (29.6 mmol) of 4-chloromethyl-2-methylquinoline hydrochloride and 5.61 g (32.6 mmol) of 4-methylsulfonylphenol in ethanol (26 mL) was added 17.1 mL (68.1 mmol) of 4 N aqueous sodium hydroxide, followed by heating under reflux for 5 hours. After standing to cool, water (150 mL) and 4 N aqueous sodium hydroxide (2.5 mL) were added and stirred for 20 minutes at room temperature. The precipitates were collected by filtration, washed thoroughly with water and hexane, and then dried at 40° C. in vacuo in the presence of phosphorus pentoxide to give 9.06 g (yield 93.5%) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline (VI-1). Its physical properties are shown below.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. temperatureto cool
  4. filtrationThe precipitates were collected by filtration
  5. washwashed thoroughly with water and hexane
  6. dry with materialdried at 40° C. in vacuo in the presence of phosphorus pentoxide

Sources & evidence

ORD record
ord-d05dd29f2db04dc4804249e9be8624c8
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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