Nitric Acid → 5-Fluoro-6-nitro-2,3-dihydro-1,3-benzoxazol-2-one

HRID 1533882Notes

Reaction equation

HRID 1533882 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[N+:12]([O-])([OH:14])=[O:13]>>[F:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 2872085-Fluoro-2(3H)-benzoxazolone

Product 1

HCID 112178355-Fluoro-6-nitro-2,3-dihydro-1,3-benzoxazol-2-one

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 300 ml concentrated nitric acid, at room temperature, was added portionwise 73.2 g (0.48 mole) of 5-fluorobenzoxazolin-2-one. The reaction mixture was warmed to 50° C., and was stirred for 4 hours. After cooling, the reaction mixture was poured onto ice. The precipitate which formed was collected, washed with water, and dried to give 72.8 g of the title compound as a brown powder: m.p. 207°-209° C.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto ice
  3. customThe precipitate which formed
  4. customwas collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-2a5138da10454a3ab481698c81bae0ea
Source dataset
uspto-grants-1992_02
Patent number
US05086062

Reaction notes

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