Ethyl 5-methylsalicylate → HCID 57756492, compound

HRID 228616Notes

Reaction equation

HRID 228616 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.[CH3:16][C:17]1[CH:27]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:20]([OH:28])=[CH:19][CH:18]=1>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:28][C:20]1[CH:19]=[CH:18][C:17]([CH3:16])=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 2

HCID 118629Ethyl 5-methylsalicylateHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 57756492HCID 57756492, compoundYield 35%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
160 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (113 mg), ethyl 5-methylsalicylate (632 mg), and 4-dimethylaminopyridine (435 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. overnight. 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, and the mixture 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, and the residue was purified by column chromatography using chloroform and by thin layer chromatography using acetone-hexane to give the title compound (64.1 mg, yield 35%).

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 mixture 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-948688492bd04c6081c308e0d706ba8e
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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