Nitric Acid → 7-fluoro-4-isobutyl-6-nitro-1,4-benzoxazin-3(4H)-one

HRID 1441101Notes

Reaction equation

HRID 1441101 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[N:6]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N+:17]([O-])([OH:19])=[O:18]>C(OC(=O)C)(=O)C.C(O)(=O)C>[F:1][C:2]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:5]2[N:6]([CH2:11][CH:12]([CH3:13])[CH3:14])[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 190471647-fluoro4-isobutyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 190471587-fluoro-4-isobutyl-6-nitro-1,4-benzoxazin-3(4H)-oneYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To 2.50 g (11.2 mmol) of 7-fluoro-4-isobutyl-2H-1,4-benzoxazin-3(4H)one in 25 ml of acetic anhydride was added dropwise over 10 min. a solution of 2.5 g (26.9 mmol) of 70% nitric acid in 5 ml of glacial acetic acid. After the addition was complete, the reaction was stirred for 1 hour at room temperature then it was quenched by pouring into 50 ml of ice/water. The resulting white precipitate was collected by vacuum filtration and dried in a vacuum oven at 60° C. overnight to yield 2.71 g (90% yield) of the desired nitrated product, m.p. 108°-110° C.

Workup

  1. additionAfter the addition
  2. customit was quenched
  3. additionby pouring into 50 ml of ice/water
  4. filtrationThe resulting white precipitate was collected by vacuum filtration
  5. customdried in a vacuum oven at 60° C. overnight
  6. customto yield 2.71 g (90% yield) of the desired nitrated product, m.p. 108°-110° C.

Sources & evidence

ORD record
ord-87f3c8b8600d40de996bf15ed8d21a1f
Source dataset
uspto-grants-1996_03
Patent number
US05502027

Reaction notes

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