Water → HCID 22132790, compound

HRID 228525Notes

Reaction equation

HRID 228525 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.[OH2:16].Cl[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1Cl>CN(C)C1C=CN=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:18]1[C:19]2[C:20](=[CH:11][CH:2]=[CH:3][CH:4]=2)[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 72391,2-DichlorobenzeneHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 22132790HCID 22132790, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
150 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (100 mg), 1-hydroxy-2-naphthonic acid (252 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (3 ml), and the suspension was stirred at 150° C. for 2 hr. The reaction solution was cooled to room temperature, water was then added thereto, 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 column chromatography using acetone-chloroform to give the title compound (119 mg, yield 80%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water and saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bf5ebc908a5e4138ac208f316525fbce
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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