Nitric Acid → HCID 13731301, compound

HRID 569693Notes

Reaction equation

HRID 569693 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:11][CH2:12][CH3:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N+:16]([O-])([OH:18])=[O:17].O>S(=O)(=O)(O)O>[F:1][C:2]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:5]2[N:6]([CH2:11][CH2:12][CH3:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 14099378HCID 14099378, compound

Product 1

HCID 13731301HCID 13731301, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-5 °C

Procedure

A stirred solution of 20.0 grams (0.096 mole) of 7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one in 100 ml of concentrated sulfuric acid was cooled to -10°C. A mixture of 10 ml of nitric acid (70% nitric acid by weight in water) and 10 ml of concentrated sulfuric acid was added dropwise during a 20 minute period. After complete addition the mixture was stirred at -5° C. for 10 minutes. The reaction mixture was poured into water which was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave a tacky solid. This solid was triturated witha mixture of diethyl ether, petroleum ether, and ethyl acetate (1:1:1) to yield, after filtration, 7.2 grams of 7-fluoro-6-nitro-4-propyl-2H-1,4-benzoxazin-3(4H)-one.

Workup

  1. additionwas added dropwise during a 20 minute period
  2. additionAfter complete addition the mixture
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customto leave a tacky solid
  8. customThis solid was triturated witha mixture of diethyl ether, petroleum ether, and ethyl acetate (1:1:1)
  9. customto yield
  10. filtrationafter filtration, 7.2 grams of 7-fluoro-6-nitro-4-propyl-2H-1,4-benzoxazin-3(4H)-one

Sources & evidence

ORD record
ord-5392c633294149edb862b26a3a7fc867
Source dataset
uspto-grants-1988_03
Patent number
US04734124

Reaction notes

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