8-Aminoquinoline → HCID 46932810, compound

HRID 1192105Notes

Reaction equation

HRID 1192105 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[NH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2>>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:21][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)=[O:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 113598-AminoquinolineHCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 46932810HCID 46932810, compound

Procedure

Prepared according to the procedure described for example 70 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (150 mg, 0.43 mmol) and 8-amino quinoline (74 mg, 0.51 mmol). The title compound was obtained as a yellow solid (20 mg, 10% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.83 (1H, m), 9.01 (3H, m), 8.83 (1H, m), 8.47 (1H, m), 8.28 (1H, m), 7.82 (1H, m), 7.66 (2H, m), 1.25 (1H, m). MS m/z: 477.23, 479.23 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e375818aa878427ca9beacc0039ead75
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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