Water → 3-Butyryl-4-(2-methylphenylamino)-8-(3-dimethylaminopropoxy)quinoline

HRID 1090657Notes

Reaction equation

HRID 1090657 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.[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36]Cl.O>CN(C)C=O>[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][CH2:36][CH2:35][CH2:34][N:33]([CH3:38])[CH3:32])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 943083-(Dimethylamino)propyl chloride hydrochloride2×HCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 99311293-Butyryl-4-(2-methylphenylamino)-8-(3-dimethylaminopropoxy)quinolineYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.20 g, 10 mmol) and potassium t-butoxide (3.05 g, 25 mmol) were dissolved in dimethyl formamide (30 ml), warmed to 80° and 3-dimethylaminopropyl chloride hydrochloride (1.90 g, 12 mmol) added. The mixture was stirred for 1 hour at 80° then a further portion of potassium t-butoxide (2.44 g, 20 mmol) and 3-dimethylaminopropyl chloride hydrochloride (1.58 g, 10 mmol) added. After a further 2 hours at 80° the mixture was poured into water, extracted with ether and the ether extracts dried and evaporated. Chromatography (silica gel, 5% methanolic ammmonia in dichloromethane) and recrystallisation from ethyl acetate gave 3-butyryl-4-(2-methylphenylamino)-8-(3-dimethylaminopropoxy)quinoline (1.80 g, 88%), m.p. 109°-110°.

Workup

  1. temperaturewarmed to 80°
  2. extractionextracted with ether
  3. dry with materialthe ether extracts dried
  4. customevaporated
  5. customChromatography (silica gel, 5% methanolic ammmonia in dichloromethane) and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-a0d99f9223a44962bdc9254f3ae77b28
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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