2-Chloro-5-nitroquinoline → N5-(1H-Indol-4-ylmethyl)-N2-(2-methyl-2,3-dihydro-benzofuran-7-yl)-quinoline-2,5-diamine

HRID 1170193Notes

Reaction equation

HRID 1170193 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](Cl)=[N:9]2)([O-])=O.[CH3:15][CH:16]1[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:24]([NH2:25])[C:18]=2[O:17]1.[NH:26]1[C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([CH:35]=O)[C:29]=2[CH:28]=[CH:27]1>>[NH:26]1[C:34]2[C:29](=[C:30]([CH2:35][NH:1][C:4]3[C:5]4[CH:6]=[CH:7][C:8]([NH:25][C:24]5[C:18]6[O:17][CH:16]([CH3:15])[CH2:20][C:19]=6[CH:21]=[CH:22][CH:23]=5)=[N:9][C:10]=4[CH:11]=[CH:12][CH:13]=3)[CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1

Participants

4

Reactant 3

HCID 3192512-Chloro-5-nitroquinolineHCID 333703Indole-4-carboxaldehydeHCID 13535826HCID 13535826, compound

Product 1

HCID 24991900N5-(1H-Indol-4-ylmethyl)-N2-(2-methyl-2,3-dihydro-benzofuran-7-yl)-quinoline-2,5-diamine

Procedure

The title compound, MS: m/e=421.4 (M+H+), was prepared from 5-nitro-2-chloroquinoline, 2,3-dihydro-2-methyl-7-benzofuranamine (CAS 26210-74-2) and indole-4-carbaldehyde as described in example 26.

Sources & evidence

ORD record
ord-b8a26f4e12ea47c59c7c2ca0083cc01f
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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