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

HRID 266151Notes

Reaction equation

HRID 266151 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[C:11]2[C:6](=[CH:7][C:8]([O:31][CH3:32])=[C:9]([O:29][CH3:30])[CH:10]=2)[N:5]=1.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>ClCCl>[CH2:33]([N:35]([CH2:2][CH2:3][C:4]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)[C:11]2[C:6](=[CH:7][C:8]([O:31][CH3:32])=[C:9]([O:29][CH3:30])[CH:10]=2)[N:5]=1)[CH2:36][CH3:37])[CH3:34]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 11799673Ethyl 2-(2-bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Product 1

HCID 19032341ethyl 2-[2-(N,N-diethylamino)ethyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-(2-bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (0.45 g), diethylamine (0.326 g) and dichloromethane (10 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-methanol (20:1, v/v) gave ethyl 2-[2-(N,N-diethylamino)ethyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (0.113 g, 26%). This compound was recrystallized from ethyl acetate - hexane. Colorless prisms, mp. 76°-78° C.

Workup

  1. temperatureunder reflux for 14 hours
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe fractions eluted with chloroform-methanol (20:1

Sources & evidence

ORD record
ord-e6e2b11bb0f543aba34e94160a6f12f4
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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