4-Nitrophenol → Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)-

HRID 1857134Notes

Reaction equation

HRID 1857134 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.[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([O-:18])=[O:17].C(=O)([O-])O.[Na+]>>[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:25][C:22]1[CH:23]=[CH:24][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 9804-NitrophenolHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 22132806Quinoline, 6,7-dimethoxy-4-(4-nitrophenoxy)-Yield 169.1%

Conditions

Temperature
170 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (1.84 g) and commercially available 4-nitrophenol (3.42 g) was mixed and stirred at 170° C. for 50 minutes. After cooling to room temperature in air, aqueous sodium hydrogen carbonate was added to the reaction mixture, and the admixture was extracted 3 times with ethyl acetate, and the ethyl acetate layer was washed with brine and then dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/methanol to obtain 4.54 g of the title compound (yield: 89%).

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe admixture was extracted 3 times with ethyl acetate
  3. washthe ethyl acetate layer was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was removed by reduced-pressure distillation
  6. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/methanol

Sources & evidence

ORD record
ord-1b276ac3de974225a2f85f254906bd73
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…