1H-indol-4-ol → HCID 22132677, compound

HRID 1857101Notes

Reaction equation

HRID 1857101 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:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[CH:20][NH:21]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:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[CH:20][NH:21]2

Participants

4

Reactant 3

HCID 754211H-indol-4-olHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 22132677HCID 22132677, compoundYield 32%

Conditions

Temperature
180 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (112 mg) and commercially available 4-hydroxyindole (200 mg) were mixed and stirred at 180° C. for 30 minutes. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate and then partitioned between water and chloroform, and the chloroform layer was dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (3/1) to obtain 51 mg of the title compound (yield: 32%).

Workup

  1. custompartitioned between water and chloroform
  2. dry with materialthe chloroform layer was dried with anhydrous magnesium sulfate
  3. customAfter removing the solvent
  4. distillationby reduced-pressure distillation
  5. customthe resulting residue was purified by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-30d73aadb5c14c7c9d4a8deb4a6a8e80
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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