4,7-Dichloroquinoline → Hydroxychloroquine, (S)-

HRID 1034163Notes

Reaction equation

HRID 1034163 reaction equation
[NH2:1][C@@H:2]([CH3:12])[CH2:3][CH2:4][CH2:5][N:6]([CH2:10][CH3:11])[CH2:7][CH2:8][OH:9].Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([Cl:24])=[CH:21][CH:22]=2)[N:17]=[CH:16][CH:15]=1.NC(C)CCCN(CC)CCO>>[CH3:11][CH2:10][N:6]([CH2:7][CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][C@@H:2]([NH:1][C:14]1[CH:15]=[CH:16][N:17]=[C:18]2[C:23]=1[CH:22]=[CH:21][C:20]([Cl:24])=[CH:19]2)[CH3:12]

Participants

4

Reactant 3

HCID 68664,7-DichloroquinolineHCID 1122882-[(4-Aminopentyl)(ethyl)amino]ethan-1-olHCID 11095130Ethanol, 2-[(4-aminopentyl)ethylamino]-, (S)-

Product 1

HCID 178396Hydroxychloroquine, (S)-

Procedure

(S)-(+)-Hydroxychloroquine was prepared by condensing (S)-(+)-2-[(4-aminopentyl)ethylamino]ethanol with 4,7-dichloroquinoline. The latter compound is known. The (S)-(+)-2-[(4-aminopentyl)ethylamino]ethanol was prepared by resolving known racemic 2-[(4-aminopentyl)ethylamino]-ethanol by forming a salt thereof with known (S)-(+)-mandelic acid and separating the (S)-(+)-mandelic acid salts of the two enantiomers by crystallization.

Workup

  1. customby forming a salt
  2. customwith known (S)-(+)-mandelic acid and separating the (S)-(+)-mandelic acid salts of the two enantiomers
  3. customby crystallization

Sources & evidence

ORD record
ord-5fb972e8a84e4214b3cb1f9b560808a8
Source dataset
uspto-grants-1994_05
Patent number
US05314894

Reaction notes

Loading…