Water → 7-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([CH:14]=1)[O:7][CH2:8][C:9](OCC)=[O:10].O>C(O)(=O)C.[Fe]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:15][C:9](=[O:10])[CH2:8][O:7][C:6]=2[CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A solution of the 49.0 grams (0.20 mole) of ethyl 2-(5-fluoro-2-nitrophenoxy)acetate in 100 ml of glacial acetic acid was added to a warm (60° C.), stirred mixture of iron powder (50.0 grams, 0.90 mole) in 300 ml of glacial acetic acid. The reaction temperature was allowed to reach 100° C., and the mixture was stirred for approximately three hours. This mixture was poured into water, forming a precipitate. The precipitate was collected by filtration and was recrystallized from ethanol to yield 25.0 grams of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one; another sample of this compound prepared in a similar manner, and then purified further, had a melting point of 205°-206° C. and an nmr spectrum which was consistent with the proposed structure.
Workup
- customto reach 100° C.
- stirringthe mixture was stirred for approximately three hours
- customforming a precipitate
- filtrationThe precipitate was collected by filtration
- customwas recrystallized from ethanol
Sources & evidence
- ORD record
- ord-d498f89c67c34a9ca9cbc1c1fb0756a8
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04734124
Reaction notes
Loading…