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

HRID 513417Notes

Reaction equation

HRID 513417 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-nitroquinoline2×HCID 10942334Sodium Methoxide

Product 1

HCID 5207735-Methoxy-8-nitroquinolineYield 233.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
81 °C

Procedure

Sodium methoxide (571 mg, 1.05 mmol) was added to a solution of 5-chloro-8-nitroquinoline (Intermediate 65) (550 mg, 2.64 mmol) in MeOH (15 ml) and heated to 81° C. for 2 h. After cooling, the mixture was concentrated in vacuo, water was added and the mixture was extracted with DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo gave the title compound (500 mg, 93%). The structure was confirmed by 1H NMR.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo, water
  3. additionwas added
  4. extractionthe mixture was extracted with DCM
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-982fdd174351443d8cd59091d8e29149
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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