Ethyl Acetate → 2,5-Dichloro-4-methoxyquinoline

HRID 430090Notes

Reaction equation

HRID 430090 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:13])[N:3]=1.[O:14]([CH3:16])[K].CCOC(C)=O>CO>[Cl:1][C:2]1[CH:11]=[C:10]([O:14][CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:13])[N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 183536682,4,5-TrichloroquinolineHCID 178502595HCID 178502595, compound

Product 1

HCID 183537032,5-Dichloro-4-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.4,5-trichloroquinoline (0.79 g, 3.4 mmol) was added KOMe (20.4 ml of a 0.5 M suspension in MeOH). The mixture was heated under reflux for 2.5 h. EtOAc was added and the solution was allowed to cool to room temperature. The solvent was evaporated in vacuo and the residue submitted to column chromatography (silica gel, EtOAc:hexanes 1:6→1:3). 4,5-Dichloro-2-methoxyquinoline eluted first, then 2,4,5-trichloroquinoline. followed by the title compound, a colourless solid, (0.43 g, 44%). δH (CDCl3) 4.04 (s, 3H), 6.77 (s, 1H), 7.50-7.60 (m, 2H), 7.85 (dd, J=6.7, 3.0, 1H); MS (AP+) 228 (MH+, 100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. customThe solvent was evaporated in vacuo
  4. wash4,5-Dichloro-2-methoxyquinoline eluted first

Sources & evidence

ORD record
ord-92851fa35ffa4a28b7a52e576c33192d
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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