2-Bromoethanol → 3-Isobutyryl-4-(2-methylphenylamino)-8-(2-hydroxyethoxy)-quinoline

HRID 1534496Notes

Reaction equation

HRID 1534496 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[OH:24])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:25][C:26](C)([O-:28])C.[K+].BrCCO>O1CCCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:24][CH2:25][CH2:26][OH:28])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 108982-Bromoethanol2×HCID 103586453-Isobutyryl-4-(2-methylphenylamino) 8-hydroxyquinolineHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 104064693-Isobutyryl-4-(2-methylphenylamino)-8-(2-hydroxyethoxy)-quinolineYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isobutyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (5 g, 15.6 mmol) in dry tetrahydrofuran (250 ml) was added potassium t-butoxide (2.63 g, 23.4 mmol), followed by 2-bromoethanol (3.9 g, 31.2 mmol). The stirred mixture was heated under reflux for 16 hours, then a further quantity of potassium t-butoxide (2.63 g, 23.4 mmol) and 2-bromoethanol (3.9 g, 31.2 mmol) added, and heating continued for 2 days. The solvent was evaporated, and the residue treated with aqueous sodium bicarbonate and extracted into dichloromethane. The extracts were dried and evaporated to an oil, which was purified by flash chromatography (silica gel, dichloromethane/methanol) and recrystallization from 40-60 petroleum ether to yield 3-isobutyryl-4-(2-methylphenylamino)-8-(2-hydroxyethoxy)-quinoline (2.25 g), m.p. 154°-156°.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureheating
  4. customThe solvent was evaporated
  5. additionthe residue treated with aqueous sodium bicarbonate
  6. extractionextracted into dichloromethane
  7. customThe extracts were dried
  8. customevaporated to an oil, which
  9. customwas purified by flash chromatography (silica gel, dichloromethane/methanol) and recrystallization from 40-60 petroleum ether

Sources & evidence

ORD record
ord-affdba173dad490f957f0361d0024645
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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