Diethylamine → HCID 54389391, compound

HRID 1684587Notes

Reaction equation

HRID 1684587 reaction equation
[Cl:1][C:2]1[C:3]([CH2:26]Cl)=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[CH:9][C:8]([O:22][CH3:23])=[C:7]([O:24][CH3:25])[CH:6]=2.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>ClCCl>[Cl:1][C:2]1[C:3]([CH2:26][N:30]([CH2:31][CH3:32])[CH2:28][CH3:29])=[N:4][C:17]2[C:12]([C:11]=1[C:10]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([O:22][CH3:23])[CH:9]=1)=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=2

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 19039886HCID 19039886, compound

Product 1

HCID 54389391HCID 54389391, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-chloro-2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (2.0 g), diethylamine (2.5 g) and dichloromethane (50 ml) was stirred under reflux for 14 hours. The reaction mixture was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform gave 3-chloro-2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (1.47 g, 67%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 146°-148° 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
  5. washThe fractions eluted with chloroform

Sources & evidence

ORD record
ord-68311386bce64d25992447d2926ae5b3
Source dataset
uspto-grants-1997_06
Patent number
US05641788

Reaction notes

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