3-Butyryl-4-chloro-8-methoxyquinoline → 1-[4-(4,6-Dimethyl-benzo[1,3]dioxol-5-ylamino)-8-methoxy-quinolin-3-yl]-butan-1-one

HRID 1090632Notes

Reaction equation

HRID 1090632 reaction equation
[CH3:1][C:2]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH3:12])[C:3]=1[NH2:4].[C:13]([C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:27]=1Cl)=[CH:25][CH:24]=[CH:23][C:22]=2[O:29][CH3:30])(=[O:17])[CH2:14][CH2:15][CH3:16]>O1CCOCC1>[C:13]([C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:27]=1[NH:4][C:3]1[C:5]([CH3:12])=[CH:6][C:7]3[O:11][CH2:10][O:9][C:8]=3[C:2]=1[CH3:1])=[CH:25][CH:24]=[CH:23][C:22]=2[O:29][CH3:30])(=[O:17])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 117775673-Butyryl-4-chloro-8-methoxyquinolineHCID 199138202,6-Dimethyl-3,4-(methylenedioxy)aniline

Product 1

HCID 102499351-[4-(4,6-Dimethyl-benzo[1,3]dioxol-5-ylamino)-8-methoxy-quinolin-3-yl]-butan-1-oneYield 433.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,6-Dimethyl-3,4-(methylenedioxy)aniline (1.67 g, 20 mmol) and 3-butyryl-4-chloro-8-methoxyquinoline (2.3 g, 10 mmol) were heated together under reflux in 1,4-dioxan (50 ml) for 2 hours. The solvent was evaporated and the residue was dissolved in dichloromethane, washed with 2M HCl, sodium hydrogen carbonate solution (×2) and brine. The organic solution was dried, filtered and evaporated to a solid which was recrystallized from ethanol to give 3-butyryl-4-(3,4-methylenedioxy-2,6-dimethylphenylamino)-8-methoxyquinoline (17 g, 43%), m.p. 150°-2° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with 2M HCl, sodium hydrogen carbonate solution (×2) and brine
  4. customThe organic solution was dried
  5. filtrationfiltered
  6. customevaporated to a solid which
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-07d8ef44442b4f6e9bc3f0c4855f2d79
Source dataset
uspto-grants-1992_01
Patent number
US05082848

Reaction notes

Loading…