Methanol → HCID 23506676, compound

HRID 1883522Notes

Reaction equation

HRID 1883522 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]([CH3:23])[CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][OH:20])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:24](Cl)(=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]/[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].CO>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]([CH3:23])[CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH3:22])[CH2:18][CH2:19][O:20][C:24](=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]/[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3652HydroxychloroquineHCID 5702750HCID 5702750, compound

Product 1

HCID 23506676HCID 23506676, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-4-[4-[ethyl(2-hydroxyethyl)amino]1-methylbutylamino]-quinoline (hydroxychloroquine) (3.17 g, 9.4 mmol) in 30 ml dichloromethane was added elaidic acid chloride (2.82 g, 9.4 mmol) and the reaction mixturewas stirred at ambient temperature for 48 hours. A small amount of methanol was added, and the solvents were evaporated at high vacuum. The residue was repeatedly purified on a column of silica gel (first run: chloroform/methanol 9:1, second run: chloroform/methanol 95:5). Homogenous fractions were evaporated to give 1.18 g (21%) of the title compound.

Workup

  1. customthe solvents were evaporated at high vacuum
  2. customThe residue was repeatedly purified on a column of silica gel (first run: chloroform/methanol 9:1, second run: chloroform/methanol 95:5)
  3. customHomogenous fractions were evaporated

Sources & evidence

ORD record
ord-537b418663ed4f5789cbd39df9c688be
Source dataset
uspto-grants-2004_07
Patent number
US06762175B2

Reaction notes

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