Water → HCID 10451656, compound

HRID 1647491Notes

Reaction equation

HRID 1647491 reaction equation
Br[CH2:2][CH2:3][OH:4].[C:5]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[CH3:27])=[CH:16][CH:15]=[CH:14][C:13]=2[OH:28])(=[O:8])[CH2:6][CH3:7].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[C:5]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[CH3:27])=[CH:16][CH:15]=[CH:14][C:13]=2[O:28][CH2:2][CH2:3][OH:4])(=[O:8])[CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 9973516HCID 9973516, compound

Product 1

HCID 10451656HCID 10451656, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 2-bromoethanol (5.75 ml, 42 mmol) in acetone (25 ml) was added dropwise to a refluxing mixture of 3-propanoyl-4-(4-fluoro-2-methylphenylamino)-8-hydroxyquinoline (1.62 g, 5 mmol), anhydrous potassium carbonate (6.9 g, 50 mmol) and acetone (25 ml) with vigorous stirring. Heating was continued for 18 hours, then water added, the product extracted into dichloromethane, dried and evaporated. Chromatography (silica gel, 2-5% methanol in dichloromethane) and recrystallisation from methanol yielded 3-propanoyl-4-(4-fluoro-2-methylphenylamino)-8-(2-hydroxyethoxy)-quinoline (0.89 g), m.p. 170°-1.72°.

Workup

  1. temperatureHeating
  2. extractionthe product extracted into dichloromethane
  3. customdried
  4. customevaporated
  5. customChromatography (silica gel, 2-5% methanol in dichloromethane) and recrystallisation from methanol

Sources & evidence

ORD record
ord-f360211953924528ab3d8f471eca31c1
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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