2-(Chloroethoxy)ethanol → 3-Butyryl-4-(2-methylphenylamino)-8-(2-(2-hydroxyethoxy)ethoxy)quinoline

HRID 1647466Notes

Reaction equation

HRID 1647466 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])[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].Cl[CH2:32][CH2:33][O:34][CH2:35][CH2:36][OH:37]>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][CH2:32][CH2:33][O:34][CH2:35][CH2:36][OH:37])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 123612-(Chloroethoxy)ethanolHCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 117421933-Butyryl-4-(2-methylphenylamino)-8-(2-(2-hydroxyethoxy)ethoxy)quinolineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (2.40 g, 7.5 mmol) and potassium t-butoxide (1.22 g, 10 mmol) were dissolved in tetrahydrofuran (40 ml), 2-(2-chloroethoxy)ethanol (1.58 ml, 15 mmol) added, and the mixture heated at reflux for 18 hours. The solvent was evaporated, the residue taken up in dichloromethane, washed with water and brine, dried and evaporated. Chromatography (silica gel, 3-5% methanol in dichloromethane) and recrystallisation from ethyl acetate gave 3-butyryl-4-(2-methylphenylamino)-8-(2-(2-hydroxyethoxy)ethoxy)quinoline (1.77 g, 60%), m.p. 144°-146°.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated
  4. washwashed with water and brine
  5. customdried
  6. customevaporated
  7. customChromatography (silica gel, 3-5% methanol in dichloromethane) and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-b0484501557f4ee8aa2394a2b22914f4
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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