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

HRID 1381642Notes

Reaction equation

HRID 1381642 reaction equation
[N+]([C:4]1[CH:13]=[C:12]([N+:14]([O-])=O)[C:11]([F:17])=[CH:10][C:5]=1[O:6][CH2:7][C:8]#[N:9])([O-])=O.C(O)(=[O:20])C>[Fe]>[F:17][C:11]1[C:12]([NH2:14])=[CH:13][C:4]2[NH:9][C:8](=[O:20])[CH2:7][O:6][C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 140535322,4-Dinitro-5-fluorophenoxyacetonitrile

Product 1

HCID 103133897-Fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-oneYield 71.7%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Iron powder (5.6 g) was suspended in 5% acetic acid (112 g), and a solution of 2,4-dinitro-5-fluorophenoxyacetonitrile (2.4 g) in acetic acid (48 g) was dropwise added thereto under reflux, followed by refluxing for an additional 1 hour. The reaction mixture was filtered, and the filtrate was extracted with ethyl acetate. The extract was concentrated, and the precipitated crystals were collected by filtration and washed with a mixture of hexane and ether to give 7-fluoro-6-amino-2H-1,4-benzoxazin-3-(4H)-one (1.3 g; yield, 71.7%).

Workup

  1. temperatureunder reflux
  2. temperatureby refluxing for an additional 1 hour
  3. filtrationThe reaction mixture was filtered
  4. extractionthe filtrate was extracted with ethyl acetate
  5. concentrationThe extract was concentrated
  6. filtrationthe precipitated crystals were collected by filtration
  7. washwashed with a mixture of hexane and ether

Sources & evidence

ORD record
ord-44f7f73e1cc840abbb0f249a85da62d4
Source dataset
uspto-grants-1989_02
Patent number
US04803270

Reaction notes

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