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

HRID 228503Notes

Reaction equation

HRID 228503 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:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:18]=1[CH:19]=[O:20]>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:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:18]=1[CH:19]=[O:20]

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

4-Chloro-6,7-dimethoxyquinoline (113 mg), 2-hydroxy-5-methylbenzaldehyde (344 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 then removed therefrom by distillation under the reduced pressure. Chloroform was added to the residue. The organic layer was washed with a 1 N aqueous sodium hydroxide solution and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by column chromatography using chloroform to give the title compound (157 mg, yield 96%).

Workup

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

Sources & evidence

ORD record
ord-c2f1d15658424d48b60144c879dde6f0
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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