2-Bromoethanol → 7-(2-Bromoethoxy)-3-cyano-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline

HRID 1784098Notes

Reaction equation

HRID 1784098 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]3[O:20][CH2:21][O:22][C:15]=13)=[CH:10][C:9]([O:23][CH3:24])=[C:8]([OH:25])[CH:7]=2)#[N:2].[Br:26][CH2:27][CH2:28]O>>[Br:26][CH2:27][CH2:28][O:25][C:8]1[CH:7]=[C:6]2[C:11]([C:12]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]4[O:20][CH2:21][O:22][C:15]=34)=[C:3]([C:1]#[N:2])[CH:4]=[N:5]2)=[CH:10][C:9]=1[O:23][CH3:24]

Participants

3

Reactant 2

HCID 108982-BromoethanolHCID 1354941593-Cyano-7-hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline

Product 1

HCID 179805137-(2-Bromoethoxy)-3-cyano-6-methoxy-4-(2,3-methylenedioxyanilino)quinolineYield 82%

Procedure

Using an analogous procedure to that described in Example 8, 3-cyano-7-hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinoline was reacted with 2-bromoethanol to give the title compound in 82% yield; NMR Spectrum: (DMSOd6) 3.88 (t, 2H), 3.94 (s, 3H), 4.51 (t, 2H), 5.96 (s, 2H), 6.8-6.93 (m, 3H), 7.34 (s, 1H), 7.8 (s, 1H), 8.42 (s, 1), 9.53 (s, 1H); Mass Spectrum: M+H+ 444.

Sources & evidence

ORD record
ord-cd01101c1137484d92df54c3e56ba1c6
Source dataset
uspto-grants-2009_03
Patent number
US07501516B2

Reaction notes

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