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

HRID 1090662Notes

Reaction equation

HRID 1090662 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.Cl[CH2:33][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CN(C)C=O.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][CH2:33][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 122962834-(3-Chloropropyl)morpholinium chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 102530533-Butyryl-4-(2-methylphenylamino)-8-(3-morpholinopropoxy)quinolineYield 58.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.2 g, 10 mmol) and potassium t-butoxide (5.0 g, 40 mmol) were stirred in dry dimethylformamide (100 ml) at 100° , then 4-(3-chloropropyl)morpholine hydrochloride (5 0 g, 14 mmol) was added. Heating was continued for 2.5 hours, then the mixture was diluted with water and extracted with ether. The combined extracts were dried and evaporated to an oily residue. Chromatography (silica gel, 3% methanolic ammonia in chloroform) and crystallisation from petroleum ether gave 3-butyryl-4-(2-methylphenylamino)-8-(3-morpholinopropoxy)quinoline (2.6 g, 58 %), m.p. 111°-113°.

Workup

  1. temperatureHeating
  2. extractionextracted with ether
  3. customThe combined extracts were dried
  4. customevaporated to an oily residue
  5. customChromatography (silica gel, 3% methanolic ammonia in chloroform) and crystallisation from petroleum ether

Sources & evidence

ORD record
ord-d36334512b474f208a3726d5f1bda470
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

Loading…