3-Butyryl-4-(2-methylphenylamino)8-hydroxyquinoline → HCID 10388048, compound

HRID 1090660Notes

Reaction equation

HRID 1090660 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[CH2:40][CH2:39][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[CH2:40][CH2:39][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 115719161-(3-chloropropyl)pyrrolidine HydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 10388048HCID 10388048, compoundYield 8.5%

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 dissolved in dry dimethylformamide (100 ml) at 100° , 1-(3-chloropropyl)pyrrolidine hydrochloride (3.6 g, 20 mmol) added, and stirring continued for 1 hour. The mixture was diluted with water and extracted with ether, and the ether extracts dried and evaporated. Chromatography (silica gel, 0-3% methanolic ammonia in chloroform) and recrystallisation from ether gave 3-butyryl-4-(2-methylphenylamino)-8-(3-(1-pyrrolidinyl)propoxy)quinoline (0.35 g, 8.5 %), m.p. 101°-103°.

Workup

  1. extractionextracted with ether
  2. dry with materialthe ether extracts dried
  3. customevaporated
  4. customChromatography (silica gel, 0-3% methanolic ammonia in chloroform) and recrystallisation from ether

Sources & evidence

ORD record
ord-10f6e8decda14413afaf23f64810a8e6
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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