5-Hydroxyindole → 4-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinoline

HRID 1857112Notes

Reaction equation

HRID 1857112 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]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2.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:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2

Participants

4

Reactant 3

HCID 160545-HydroxyindoleHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 221326454-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinolineYield 63%

Conditions

Temperature
150 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (1.0 g) and commercially available 5-hydroxyindole (1.19 g) were mixed and stirred at 150° C. for 1.5 hours. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate and then partitioned between water and ethyl acetate, and the ethyl acetate layer was washed with brine and then dried with anhydrous sodium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel eluting in sequence with hexane/ethyl acetate, chloroform and chloroform/methanol, to obtain 898 mg of the title compound (yield: 63%).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washthe ethyl acetate layer was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customAfter removing the solvent
  5. distillationby reduced-pressure distillation
  6. customthe resulting residue was purified by column chromatography on silica gel eluting in sequence with hexane/ethyl acetate, chloroform and chloroform/methanol

Sources & evidence

ORD record
ord-624fba34fdd5417b9b33173b88d9faf7
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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