Water → HCID 10477403, compound

HRID 1090658Notes

Reaction equation

HRID 1090658 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+].Cl.[CH3:33][N:34]([CH3:39])[CH2:35][CH2:36][CH2:37]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][C:20]([F:23])=[CH:19][C:18]=1[CH3:24])=[CH:13][CH:12]=[CH:11][C:10]=2[O:25][CH2:37][CH2:36][CH2:35][N:34]([CH3:39])[CH3:33])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 943083-(Dimethylamino)propyl chloride hydrochloride3×HCID 9997267HCID 9997267, compoundHCID 23665647Potassium tert-butoxide3×

Product 1

HCID 10477403HCID 10477403, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Butyryl-4-(4-fluoro-2-methylphenylamino)-8-hydroxyquinoline (3.38 g, 10 mmol) and potassium t-butoxide (3.05 g, 25 mmol) were dissolved in dimethyl formamide (30 ml), warmed to 70° 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, and stirring continued overnight. A third portion of potassium t-butoxide (2.44 g, 20 mmol) and 3-dimethylaminopropyl chloride hydrochloride (1.58 g, 10 mmol) was added and the temperature raised to 85° . After a further 5 hours the mixture was poured into water, extracted with ether and the ether extracts dried and evaporated. Chromatography (silica gel, 4-6% methanolic ammmonia in dichloromethane) and recrystallisation from ethyl acetate gave 3-butyryl-4-(4-fluoro-2-methylphenyl-amino)-8-(3-dimethylaminopropoxy)quinoline (0.46 g, 11%), m.p. 99°-100°.

Workup

  1. temperaturewarmed to 70°
  2. stirringstirring continued overnight
  3. temperaturethe temperature raised to 85°
  4. extractionextracted with ether
  5. dry with materialthe ether extracts dried
  6. customevaporated
  7. customChromatography (silica gel, 4-6% methanolic ammmonia in dichloromethane) and recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-d96e287cdd3f495798610df65a025131
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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