Water → HCID 57756359, compound

HRID 228533Notes

Reaction equation

HRID 228533 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][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2.O>CN(C)C1C=CN=CC=1.CC1C=CC=CC=1C>[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][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2

Participants

6

Reactant 3

HCID 962WaterHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylateHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 57756359HCID 57756359, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

4-Chloro-6,7-dimethoxyquinoline (362 mg), ethyl 5-hydroxy-1H-2-indolecarboxylate (277 mg), and 4-dimethylaminopyridine (195 mg) were suspended in o-xylene, and the suspension was heated under reflux overnight. 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 saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using ethyl acetate-hexane on silica gel to give the title compound (161 mg, yield 30%).

Workup

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

Sources & evidence

ORD record
ord-f385e284c5e54573a3b3343d24475ffb
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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