2-(2-(2-Chloroethoxy)ethoxy)ethanol → HCID 10095388, compound

HRID 1647467Notes

Reaction equation

HRID 1647467 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][O:37][CH2:38][CH2:39][OH:40]>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][O:37][CH2:38][CH2:39][OH:40])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 788712-(2-(2-Chloroethoxy)ethoxy)ethanolHCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 23665647Potassium tert-butoxide

Product 1

HCID 10095388HCID 10095388, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (2.40 g, 7.5 mmol), potassium t-butoxide (1.22 g, 10 mmol) and 2-(2-(2-(chloroethoxy)ethoxy)ethanol (2.18 ml, 15 mmol) in tetrahydrofuran (40 ml) was heated at reflux for 3 days. The solvent was evaporated, the residue taken up in dichloromethane, washed with water and brine, dried and evaporated. Chromatography (silica gel, 0-10% methanol in ethyl acetate) and crystallisation from ether gave 3-butyryl-4-(2-methylphenylamino)-8-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)quinoline (2.32 g, 68%) as a hygroscopic solid, m.p. 102°-104°.

Workup

  1. temperatureat reflux for 3 days
  2. customThe solvent was evaporated
  3. washwashed with water and brine
  4. customdried
  5. customevaporated
  6. customChromatography (silica gel, 0-10% methanol in ethyl acetate) and crystallisation from ether

Sources & evidence

ORD record
ord-20f74809e27449aeb95a4968a96d5786
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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