Sodium Hydroxide → (2-Chloro-4-methylquinolin-6-yl)methanol

HRID 1666698Notes

Reaction equation

HRID 1666698 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([Cl:13])[CH:7]=[C:6]2[CH3:14].[OH-:15].[Na+]>CSC.C(OCC)(=O)C>[Cl:13][C:8]1[CH:7]=[C:6]([CH3:14])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][OH:15])[CH:4]=2)[N:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14991293HCID 14991293, compound

Product 1

HCID 57970169(2-Chloro-4-methylquinolin-6-yl)methanol

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-bromomethyl-2-chloro-4-methylquinoline (0.39 g) in dimethyl sulfide (5 mL) was added 1 M aqueous sodium hydroxide (5 mL) at room temperature, and the mixture was stirred at 70° C. for 1 h. After cooled to room temperature, the reaction solution was diluted with ethyl acetate. The organic layer was washed with saturated brine, the organic layer was dried with anhydrous magnesium sulfate, then the desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=3:1−ethyl acetate/hexane/chloroform=1:3:1−ethyl acetate) to obtain (2-chloro-4-methylquinolin-6-yl)methanol (0.14 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  4. customthe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=3:1−ethyl acetate/hexane/chloroform=1:3:1−ethyl acetate)

Sources & evidence

ORD record
ord-2b102a638a104a5c9ead2abe259b805c
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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