2-Bromoethanol → HCID 11740620, compound

HRID 1647482Notes

Reaction equation

HRID 1647482 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][C:20]([F:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[OH:25])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH3:26][C:27](C)([O-:29])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][C:20]([F:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:25][CH2:26][CH2:27][OH:29])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 108982-Bromoethanol2×HCID 10020017HCID 10020017, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 11740620HCID 11740620, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-isobutyryl-4-(4-fluoro-2-methyl-phenylamino)-8-hydroxyquinoline (5 g, 14.8 mmol) in dry tetrahydrofuran (250 ml) was added potassium t-butoxide (2.49 g, 22.2 mmol), followed by 2-bromoethanol (3.69 g, 29.6 mmol). The stirred mixture was heated under reflux for 16 hours, then a further quantity of potassium t-butoxide (2.49 g, 22.2 mmol) and 2-bromoethanol (3.69 g, 29.6 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 recrystallisation from ether to yield 3-isobutyryl-4-(4-fluoro-2-methylphenylamino-8-(2-hydroxyethoxy) (1.97 g), m.p. 183°-185°.

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 recrystallisation from ether
  10. customto yield 3-isobutyryl-4-(4-fluoro-2-methylphenylamino-8-(2-hydroxyethoxy) (1.97 g), m.p. 183°-185°

Sources & evidence

ORD record
ord-921ec522be5a4871b2587249dfde6672
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

Loading…