ethyl 6-(N,N-diethylamino)-3-oxohexanoate → ethyl 2-[3-(N,N-diethylamino)propyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

HRID 266149Notes

Reaction equation

HRID 266149 reaction equation
Cl.[NH2:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)=O.[CH2:25]([N:27]([CH2:30][CH2:31][CH2:32][C:33](=O)[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:28][CH3:29])[CH3:26]>C(O)C>[CH2:25]([N:27]([CH2:30][CH2:31][CH2:32][C:33]1[C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=2)[C:4]2[C:3](=[CH:20][C:19]([O:21][CH3:22])=[C:18]([O:23][CH3:24])[CH:17]=2)[N:2]=1)[CH2:28][CH3:29])[CH3:26]

Participants

4

Reactant 2

HCID 19032338ethyl 6-(N,N-diethylamino)-3-oxohexanoateHCID 214661342-Amino-3',4',4,5-tetramethoxybenzophenone hydrochloride

Product 1

HCID 19032363ethyl 2-[3-(N,N-diethylamino)propyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylateYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone hydrochloride (7.7 g), ethyl 6-(N,N-diethylamino)-3-oxohexanoate (5.0 g) and ethanol (100 ml) was stirred under reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in chloroform. The chloroform layer was washed with an aqueous saturated solution of sodium bicarbonate and water and dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-methanol (20:1, v/v) gave ethyl 2-[3-(N,N-diethylamino)propyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (1.51 g, 14%). This compound was recrystallized from ethanol-hexane. Colorless prisms, mp. 96°-98° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe chloroform layer was washed with an aqueous saturated solution of sodium bicarbonate and water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. washThe fractions eluted with chloroform-methanol (20:1

Sources & evidence

ORD record
ord-b2f55d19a0fb4d078104a328740f906a
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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