Benzaldehyde, 2-hydroxy-5-methyl- → HCID 23078271, compound

HRID 228721Notes

Reaction equation

HRID 228721 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5].Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][CH:13]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:24][CH3:25])[N:15]=[CH:14][CH:13]=[C:12]2[O:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 69184Benzaldehyde, 2-hydroxy-5-methyl-HCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 23078271HCID 23078271, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
160 °C

Procedure

2-Hydroxy-5-methyl-benzaldehyde (344 mg), 4-chloro-6,7-dimethoxyquinoline (113 mg), and 4-dimethylaminopyridine (313 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 2 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with aqueous sodium hydroxide solution and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform to give 2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methyl-benzaldehyde (157 mg, yield 96%).

Workup

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

Sources & evidence

ORD record
ord-f8b258881a804681ac4aa0c38b334b2a
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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