Water → 3-[(6,7-Dimethoxy-4-quinolyl)oxy]-6-nitrobenzaldehyde

HRID 228534

Reaction equation

HRID 228534 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:18]=[CH:19][C:20]([N+:25]([O-:27])=[O:26])=[C:21]([CH:24]=1)[CH:22]=[O:23].O>ClC1C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:16][C:17]1[CH:24]=[C:21]([C:20]([N+:25]([O-:27])=[O:26])=[CH:19][CH:18]=1)[CH:22]=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 859454883-[(6,7-Dimethoxy-4-quinolyl)oxy]-6-nitrobenzaldehydeYield 66.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

4-Chloro-6,7-dimethoxyquinoline (200 mg) and 5-hydroxy-2-nitrobenzaldehyde (299 mg) were suspended in chlorobenzene (2 ml), and the suspension was heated under reflux for 8 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using ethyl acetate-hexane to give 3-[(6,7-dimethoxy-4-quinolyl)oxy]-6-nitrobenzaldehyde (210 mg, yield 66%).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 8 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was then washed with water and saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. distillationby distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-9f9db6638eed432e8ceecc30be452070
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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