HCID 20133425, compound → 6-Fluoro-2H-1,4-benzoxazin-3(4H)-one

HRID 845049Notes

Reaction equation

HRID 845049 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8](OCC)=[O:9])=[C:4]([N+:15]([O-])=O)[CH:3]=1>CO.[Ni]>[F:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][CH2:7][C:8](=[O:9])[NH:15][C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 20133425HCID 20133425, compound

Product 1

HCID 3028976-Fluoro-2H-1,4-benzoxazin-3(4H)-oneYield 88.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 46 g of ethyl 4-fluoro-2-nitrophenoxyacetate, prepared in Example 18, in 500 ml of methanol is hydrogenated under atmospheric pressure in the presence of Raney nickel. After absorption of the theoretical quantity of hydrogen, the catalyst is filtered off, the solution is concentrated in vacuo and the residue is taken up in either, from which it crystallizes. The crystals formed are filtered off, washed with ether and dried. 28 g of 6-fluoro-2H-1,4-benzoxazin-3(4H)-one are thus obtained in the form of crystals of melting point 206°-207° C.

Workup

  1. customAfter absorption of the theoretical quantity of hydrogen
  2. filtrationthe catalyst is filtered off
  3. concentrationthe solution is concentrated in vacuo
  4. customcrystallizes
  5. customThe crystals formed
  6. filtrationare filtered off
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-5143396895a348108eed13b8051e5381
Source dataset
uspto-grants-1988_07
Patent number
US04755509

Reaction notes

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