5-Chloro-8-nitroquinoline → 5-Methoxy-8-nitroquinoline

HRID 513817Notes

Reaction equation

HRID 513817 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2>CO>[CH3:1][O:2][C:5]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

4

Reactant 2

HCID 2427555-Chloro-8-nitroquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 5207735-Methoxy-8-nitroquinolineYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

NaOMe (570 mg, 10.5 mmol) was added to a solution of 5-chloro-8-nitroquinoline 27 (550 mg, 2.64 mmol) in MeOH (15 ml) and the mixture was heated at 80° C. for 2 h. The solvent was removed in vacuo and the residue was diluted with water and the aqueous phase was extracted with DCM. The organic phase was washed with brine and concentrated in vacuo to give the title compound (500 mg, 93%) which was used in the next step without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionthe aqueous phase was extracted with DCM
  4. washThe organic phase was washed with brine
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-054285ac6f3a477ea97371dce9033cd5
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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