Novoldiamine → Chloroquine

HRID 905110

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.[CH2:13]([N:15]([CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH:19]([NH2:21])[CH3:20])[CH3:14]>>[CH3:14][CH2:13][N:15]([CH2:16][CH2:17][CH2:18][CH:19]([NH:21][C:6]1[CH:7]=[CH:8][N:9]=[C:10]2[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=12)[CH3:20])[CH2:22][CH3:23]

Participants

Reactant 2

HCID 78953Novoldiamine

HCID 889747-Chloro-2,3-dihydro-4-quinolone

Product 1

HCID 2719ChloroquineYield 98.05%

Procedure

17.904 millimols, i.e. a yield of 98.05% relative to the 7-chloro-1,2,3,4-tetrahydroquinolin-4-one converted, and a yield of 96.86% relative to the 1-diethylamino-4-amino-pentane converted, and

Sources & evidence

ORD record: ord-1c186e50dfba478a90969864574abdf5
Source dataset: uspto-grants-1983_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04421920

Linked notes

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