Hydrogen Peroxide → HCID 178526455, compound

HRID 535208Notes

Reaction equation

HRID 535208 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=CC=[CH:7]2)([O-:3])=[O:2].F[C:15](F)(F)[C:16]([OH:18])=O.[OH:21]O>O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N+:10]([O-:21])=[C:16]([OH:18])[CH:15]=[CH:7]2.[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N+:10]([O-:21])=[C:16]([OH:18])[CH:15]=[CH:7]2)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 119456-Nitroquinoline

Product 2

HCID 178507287HCID 178507287, compoundHCID 178526455HCID 178526455, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-amino-2-hydroxyquinoline-N-oxide was prepared as follows. A solution of 25 g 6-nitroquinoline, 560 g of trifluoroacetic acid, and 60 g of 30% hydrogen peroxide was heated at reflux for 6 hr. After checking for the absence of peroxides, the mixture was cooled and poured into 3750 mL of water. The product was collected by filtration, washed with water and dried under vacuum at 60° C., to give 6-nitro-2-hydroxyquinoline-N-oxide (5.48 g, 19% yield). 1HNMR data for this compound (DMSO) was as follows: δ 8.8 (s, 1H), 8.4 (d, 1H), 8.1 (d, 1H), 7.8 (d, 1H), 6.9 (d, 1H).

Workup

  1. temperatureat reflux for 6 hr
  2. temperaturethe mixture was cooled
  3. filtrationThe product was collected by filtration
  4. washwashed with water
  5. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-d80cde119a474338828facaf50955c41
Source dataset
uspto-grants-2014_10
Patent number
US08858695B2

Reaction notes

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