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

HRID 1995319Notes

Reaction equation

HRID 1995319 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-: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 707846-Fluoro-2-methylquinolineHCID 23668193Sodium Nitrite

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. To this mixture was added about 0.1 g of sodium nitrite, 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 and poured into 3 gallons of ice. The mixture was basified with ammonium hydroxide, with cooling. The precipitated solid was separated by filtration, then dissolved in about two liters of warm toluene. The solution as dried over magnesium sulfate, filtered and evaporated to provide the 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 as dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-1d9b30ea89ae4c63ab43bef7f53f5396
Source dataset
uspto-grants-1983_09
Patent number
US04404207

Reaction notes

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