Dimethylamine → 5-Nitro-6-dimethylaminoquinoline

Reaction equation

[N+:1]([C:4]1[C:13](Cl)=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>>[N+:1]([C:4]1[C:13]([N:16]([CH3:17])[CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2]

Participants

Reactant 2

HCID 674Dimethylamine

HCID 40708006-Chloro-5-nitroquinoline

Product 1

HCID 190278695-Nitro-6-dimethylaminoquinoline

Procedure

5-Nitro-6-chloroquinoline, prepared as described by Manske & Kulka, Organic Reactions, Vol. VII, 59 (1953) and Campbell et al., J. Am. Chem. Soc., 68, 1559 (1946), was allowed to react with dimethylamine to yield 5-nitro-6-dimethylaminoquinoline. This material was converted to the title compound by the procedure described in Example 33.

Sources & evidence

ORD record: ord-aaeee53c8bd74854b4c49490fa0f8acd
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05656634

Reaction notes

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