Nitroxoline → 5-Amino-8-hydroxyquinoline

HRID 658451Notes

Reaction equation

HRID 658451 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.NC1C=CC(O)=CC=1F>>[NH2:12][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

3

Reactant 2

HCID 19910NitroxolineHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 4160025-Amino-8-hydroxyquinolineYield 57%

Procedure

This compound was prepared from 8-hydroxy-5-nitroquinoline (5.0 g, 26.3 mmol) in the manner described for 4-amino-3-fluorophenol, affording 2.4 g (51.3%) of 5-amino-8-hydroxyquinoline. TLC (5% MeOH/DCM), Rf=0.52.

Sources & evidence

ORD record
ord-1507a0dd847d4b5abdeed4758b6e6078
Source dataset
uspto-grants-2011_12
Patent number
US08076488B2

Reaction notes

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