2-Chloroethyl methyl ether → HCID 10340699, compound

HRID 1647479Notes

Reaction equation

HRID 1647479 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])[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].[CH3:32][O:33][CH2:34][CH2:35]Cl>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][CH2:35][CH2:34][O:33][CH3:32])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 123162-Chloroethyl methyl etherHCID 9997267HCID 9997267, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10340699HCID 10340699, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-butyryl-4-(4-fluoro-2-methylphenyl-amino)-8-hydroxyquinoline (3.38 g,. 10 mmol) and potassium t-butoxide (1.68 g, 15 mmol) in tetrahydrofuran (75 ml) was warmed to near boiling, chloroethyl methyl ether (1.83 ml, 20 mmol) added, and the mixture heated at reflux for 3 days. The solvent was evaporated then the product taken up in dichloromethane, washed with water and brine, dried and evaporated. Chromatography (silica gel, ethyl acetate/2% acetic acid/0-5% methanol) and recrystallisation from ethyl acetate/petroleum ether gave 3-butyryl-4-(4-fluoro-2-methylphenylamino)-8-(2-methoxyethoxy)quinoline (0.41 g), m.p. 124°-5°.

Workup

  1. additionadded
  2. temperaturethe mixture heated
  3. temperatureat reflux for 3 days
  4. customThe solvent was evaporated
  5. washwashed with water and brine
  6. customdried
  7. customevaporated
  8. customChromatography (silica gel, ethyl acetate/2% acetic acid/0-5% methanol) and recrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-4ffb9b6130c54216a60e9f909a8a013b
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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