Nitric Acid → Quinoline, 8-fluoro-5-nitro-

HRID 2292249Notes

Reaction equation

HRID 2292249 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[F:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2>O>[N+:1]([C:14]1[CH:13]=[CH:12][C:11]([F:10])=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[N:19]2)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 67856Quinoline, 8-fluoro-

Product 1

HCID 154498Quinoline, 8-fluoro-5-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 ml of nitric acid were added with stirring at -5° C. to 30 ml of concentrated sulfuric acid and then 16 g of 8-fluoroquinoline were added thereto with stirring over 30 minutes at -5° to 0° C. The mixture was stirred at 0° C. for three hours and was then allowed to return to room temperature. The mixture was stirred at room temperature for two hours and was then poured into a mixture of water and ice. The mixture was vacuum filtered and the product was suspended in water. The mixture was made alkaline by addition of 10% sodium carbonate solution and was extracted with methylene chloride. The organic phase was dried and evaporated to dryness under reduced pressure to obtain 12 g of 5-nitro-8-fluoro-quinoline melting at 132°-133° C.

Workup

  1. stirringThe mixture was stirred at 0° C. for three hours
  2. customto return to room temperature
  3. stirringThe mixture was stirred at room temperature for two hours
  4. filtrationfiltered
  5. additionby addition of 10% sodium carbonate solution
  6. extractionwas extracted with methylene chloride
  7. customThe organic phase was dried
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1f2f85a6bcea4416be211814fa08fa42
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Reaction notes

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