3-Butyryl-4-(2-methylphenylamino)8-hydroxyquinoline → 3-Butyryl-4-(2-methylphenylamino)-8-(2-methoxy-ethoxy)quinoline

HRID 1647443Notes

Reaction equation

HRID 1647443 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+].C1(S(O[CH2:41][CH2:42][O:43][CH3:44])(=O)=O)C=CC=CC=1>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][CH2:41][CH2:42][O:43][CH3:44])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 111952842-Methoxyethyl benzenesulfonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 117403953-Butyryl-4-(2-methylphenylamino)-8-(2-methoxy-ethoxy)quinolineYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.20 g, 10 mmol) and potassium t-butoxide (1.47 g, 12 mmol) in dry tetrahydrofuran (100 ml) was heated at reflux for 5 minutes, then 2-methoxyethyl benzenesulphonate (4.33 g, 20 mmol) added and hearing continued for 18 hours. Evaporation of the solvent, chromatography (silica gel, 1-2% methanol in dichloromethane) and recrystallisation from ethyl acetate gave 3-butyryl-4-(2-methylphenylamino)-8-(2-methoxy-ethoxy)quinoline (1.42 g, 38%), m.p. 75°-77°.

Workup

  1. temperatureat reflux for 5 minutes
  2. customEvaporation of the solvent, chromatography (silica gel, 1-2% methanol in dichloromethane) and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-03d2fb24306a4dd6b9c8534e684d301b
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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