4,7-Dichloro-8-nitroquinoline → 7-Chloro-4-methoxy-8-nitro-quinoline

HRID 513420Notes

Reaction equation

HRID 513420 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:14]2[C:9](=[C:10]([N+:16]([O-:18])=[O:17])[C:11]([Cl:15])=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1>CO>[Cl:15][C:11]1[C:10]([N+:16]([O-:18])=[O:17])=[C:9]2[C:14]([C:5]([O:2][CH3:1])=[CH:6][CH:7]=[N:8]2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 2201774,7-Dichloro-8-nitroquinoline2×HCID 10942334Sodium Methoxide

Product 1

HCID 681834397-Chloro-4-methoxy-8-nitro-quinolineYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (2.0 g, 37.0 mmol) was added to a solution of 4,7-dichloro-8-nitro-quinoline (Intermediate 68) (3.0 g, 12.3 mmol) in MeOH (20 ml) and the reaction was heated under reflux for 24 h. The solvent was removed in vacuo. The residue was dissolved in EtOAc (150 ml) and washed with water, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by column chromatography with EtOAc/heptane (4:1) to give the title compound (2.54 g, 83%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 24 h
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in EtOAc (150 ml)
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by column chromatography with EtOAc/heptane (4:1)

Sources & evidence

ORD record
ord-5e2519145ddf45159096887159a6f22f
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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