Water → HCID 10023371, compound

HRID 1090659Notes

Reaction equation

HRID 1090659 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]([CH3:37])[CH2:34][CH2:35]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][CH2:35][CH2:34][N:33]([CH3:37])[CH3:32])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 10023371HCID 10023371, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 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 at 80° and 2-dimethylaminoethyl chloride hydrochloride (2.9 g, 20 mmol) added. The mixture was stirred for 2 hours, poured into water and extracted with ether. The extracts were dried and evaporated. Chromatography (silica gel, 3-5% methanolic ammonia in dichloromethane) and recrystallisation from ether gave 3-butyryl-4-(2-methylphenylamino)-8-(2-dimethylaminoethoxy)quinoline (1.0 g, 34%), m.p. 88°-90°.

Workup

  1. extractionextracted with ether
  2. customThe extracts were dried
  3. customevaporated
  4. customChromatography (silica gel, 3-5% methanolic ammonia in dichloromethane) and recrystallisation from ether

Sources & evidence

ORD record
ord-53eea0200ac348eb9443bf7e75ea306d
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

Loading…