Nitric Acid → 7-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 1030960Notes

Reaction equation

HRID 1030960 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[F:1][C:2]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 137312977-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine (2.0 gram) in 80% aqueous sulfuric acid (30 ml) is cooled to 0° to 5° C., and 60% nitric acid (1.6 g) is gradually added thereto at 0° to 5° C. The resultant mixture is stirred at the same temperature for 30 minutes and poured onto ice water. The precipitated crystals are collected by filtration, washed with water and dried to give 7-fluoro-3,4-dihydro-3-oxo-6-nitro-2H-1,4-benzoxazine.

Workup

  1. customat 0° to 5° C
  2. additionpoured onto ice water
  3. filtrationThe precipitated crystals are collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d029f7f79e154f1d93f45f391aeb1880
Source dataset
uspto-grants-1992_04
Patent number
US05108488

Reaction notes

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