Nitric Acid → HCID 23262449, compound

HRID 2245288Notes

Reaction equation

HRID 2245288 reaction equation
[N+:1]([O-:4])(O)=[O:2].[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([OH:15])[CH:6]=1.[OH-].[Na+]>O>[N+:1]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[C:7]([OH:15])[CH:6]=[N:5]2)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 113763-HydroxyquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 23262449HCID 23262449, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of concentrated sulfic acid is added concentrated nitric acid dropwise at −30° C. Quinolin-3-ol is added to the mixture at −30° C., and then stirred at 30° C. for 2 hours. After cooled to ambient temperature, the mixture is poured into water and then neutralized with aqueous 4N sodium hydroxide solution. After extracted with ethyl acetate, the organic layer is dried, filtered and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to provide 5-nitroquinolin-3-ol.

Workup

  1. temperatureAfter cooled to ambient temperature
  2. extractionAfter extracted with ethyl acetate
  3. customthe organic layer is dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1bdf16e0ab994bd1aaad8ca6e9011c81
Source dataset
uspto-grants-2010_03
Patent number
US07683076B2

Reaction notes

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