4-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile → 4-(6-Chloro-4-iodo-2,3-methylenedioxyan ilino)-3-cyano-6,7-dimethoxyquinoline

HRID 347425Notes

Reaction equation

HRID 347425 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[Cl:18][C:19]1[C:24]([NH2:25])=[C:23]2[O:26][CH2:27][O:28][C:22]2=[C:21]([I:29])[CH:20]=1>>[Cl:18][C:19]1[C:24]([NH:25][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:16]#[N:17])=[C:23]2[O:26][CH2:27][O:28][C:22]2=[C:21]([I:29])[CH:20]=1

Participants

3

Reactant 2

HCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrileHCID 179805275-Chloro-7-iodo-1,3-benzodioxol-4-amine

Product 1

HCID 179805104-(6-Chloro-4-iodo-2,3-methylenedioxyan ilino)-3-cyano-6,7-dimethoxyquinolineYield 72.6%

Procedure

Using an analogous procedure to that described in the portion of Example 1 that is concerned with the preparation of starting materials, 4-chloro-3-cyano-6,7-dimethoxyquinoline (1.74 g) was reacted with 6-chloro-4-iodo-2,3-methylenedioxyaniline (2.5 g) to give 4-(6-chloro-4-iodo-2,3-methylenedioxyanilino)-3-cyano-6,7-dimethoxyquinoline as a solid (2.59 g) which gave the following characterising data; NMR Spectrum: (DMSOd6) 4.0 (s, 6H), 6.18 (s, 2H), 7.38 (s, 1H), 7.48 (s, 1H), 7.88 (s, 1H), 8.44 (s, 1H), 9.45 (s, 1H); Mass Spectrum: M+H+ 510.

Sources & evidence

ORD record
ord-9b2e43c34ee24c14b92906835591507e
Source dataset
uspto-grants-2007_02
Patent number
US07173135B2

Reaction notes

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