Nitric Acid → 6-Fluoro-2-methyl-5-nitroquinoline

HRID 435115

Reaction equation

HRID 435115 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10]2.[N+:18]([O-])([O-:20])=[O:19].[Na+].[N+]([O-])(O)=O.[OH-].[NH4+]>>[F:6][C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10]2

Participants

6

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 24268Sodium NitrateHCID 707846-Fluoro-2-methylquinoline

Product 1

HCID 27483306-Fluoro-2-methyl-5-nitroquinoline

Conditions

Temperature
20 °C

Procedure

To 3.5 l of fuming sulfuric acid was added, with cooling, 600 g (3.73 moles) of 6-fluoroquinaldine in small portions. About 0.1 g of sodium nitrate was added to the mixture, followed by the dropwise addition of 261 ml of fuming red nitric acid over a six-hour period while maintaining the temperature at 5°-10° C. The mixture was stirred at 20° C. for sixteen hours, then poured into 3 gallons of ice. The mixture was basified with ammonium hydroxide with cooling. The precipitated solid was separated by filtration and dissolved in about two liters of warm toluene. The solution was dried over magnesium sulfate, filtered and evaporated to provide a yellow solid, 6-fluoro-5-nitroquinaldine, m.p. 105°-108° C., which was recrystallized from 1,2-dichloroethane. The structural assignment was confirmed by nuclear magnetic resonance and infrared spectral analyses.

Workup

  1. temperaturewith cooling
  2. temperaturewhile maintaining the temperature at 5°-10° C
  3. temperaturewith cooling
  4. customThe precipitated solid was separated by filtration
  5. dissolutiondissolved in about two liters of warm toluene
  6. dry with materialThe solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-bb893f3728814c6cb64b7cddc2146ab9
Source dataset
uspto-grants-1983_08
Patent number
US04400386

Linked notes

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