2,4-Dichloroquinoline → 4-Chloro-2-methoxyquinoline

HRID 333054

Reaction equation

HRID 333054 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O-:14].[Na+]>C1(C)C=CC=CC=1>[Cl:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([O:14][CH3:13])[CH:11]=1

Participants

4

Reactant 2

HCID 6075032,4-DichloroquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 109653774-Chloro-2-methoxyquinolineYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of (2.5 g, 12.6 mmol) 2,4-dichloro-quinoline in anhydrous toluene (20 ml) was added a suspension of solid sodium methoxide (2.5 g, 46.3 mmol) in anhydrous toluene (20 ml). The mixture was stirred under reflux for 16 hours and then allowed to cool to room temperature. The solid that had formed was filtered off and washed with 50 ml toluene. The filtrate was evaporated to dryness under reduced pressure to yield a red solid (2.1 g, 10.8 mmol, 86%). MS (ES) m/z=193.1 [M+H]+.

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe solid that had formed
  3. filtrationwas filtered off
  4. washwashed with 50 ml toluene
  5. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-48e1dd726a364dd0af1d0b5699513a2f
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Linked notes

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