Hydrogen Peroxide → 6-Fluoro-8-nitroquinolin-3-ol

HRID 593351Notes

Reaction equation

HRID 593351 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[OH:15]O>C(O)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[N:8]=[CH:7][C:6]([OH:15])=[CH:5]2

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 154273Quinoline, 6-fluoro-8-nitro-

Product 1

HCID 681080436-Fluoro-8-nitroquinolin-3-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 6-fluoro-8-nitro-quinoline (900 mg, 4.7 mmol) in acetic acid (10 ml) was treated at room temperature with hydrogen peroxide (30% in water (1.6 ml), then it was stirred at 70° C. for 5 hours. For the workup, the reaction mixture was cooled and poured into ice-water. The precipitate was filtered, washed with water, collected and dried. 6-Fluoro-8-nitro-quinolin-3-ol was obtained as a brown solid (285 mg, 29%); (calculated) C9H5FN2O3 [208.2]; (found) [M−H]−=207.

Workup

  1. temperatureFor the workup, the reaction mixture was cooled
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-5859934e03294e56ae6ad93d35871dab
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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