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Water → 2-[(6,7-Dimethoxy-4-quinolyl)oxy]naphthalene-1-carbaldehyde

HRID 228538
Notes
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Reaction equation

HRID 228538 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:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]=1[CH:27]=[O:28].O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[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:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]=1[CH:27]=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 128192-Hydroxy-1-naphthaldehydeHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 230784822-[(6,7-Dimethoxy-4-quinolyl)oxy]naphthalene-1-carbaldehydeYield 15%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 7239
1,2-Dichlorobenzene
Solvent

Conditions

Temperature
160 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (100 mg), 2-hydroxy-1-naphthoaldehyde (231 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (6 ml), and the suspension was stirred at 160° C. for 2 hr. 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 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 (24 mg, yield 15%).

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-3eda3425b3e0483e83bac2f7ede96c50
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes