6-Aminoquinoline → HCID 60207404, compound

HRID 1192189Notes

Reaction equation

HRID 1192189 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]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][CH:26]=[CH:25]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]=[C:24]3[C:29](=[CH:30][CH:31]=2)[N:28]=[CH:27][CH:26]=[CH:25]3)=[O:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 113736-AminoquinolineHCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 60207404HCID 60207404, 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 6-aminoquinoline (73.7 mg, 0.51 mmol). The title compound was obtained as a yellow solid (52 mg, 25% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.84 (1H, br), 9.02 (2H, m), 8.825 (1H, m), 8.81 (1H, m), 8.34 (1H, m), 8.32 (1H, m), 8.04 (1H, m), 7.97 (1H, m), 7.51 (1H, m). MS m/z: 475.18, 477.09 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-041cde3c49fa436286032308ccaed5aa
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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