N-(4-chloro-2-fluoro-5-nitrophenyl)acetamide → N-(5-amino-4-chloro-2-fluorophenyl)acetamide
Reaction equation
[C:1]([NH:4][C:5]1[C:10]([F:11])=[CH:9][C:8]([Cl:12])=[C:7]([N+:13]([O-])=O)[CH:6]=1)(=[O:3])[CH3:2]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[C:1]([NH:4][C:5]1[C:10]([F:11])=[CH:9][C:8]([Cl:12])=[C:7]([NH2:13])[CH:6]=1)(=[O:3])[CH3:2]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
Iron powder (31.9 g) were suspended in a 5% acetic acid solution (60 ml), and the suspension was heated to 90° C. A solution of 4-(N-acetylamino)-1-chloro-5-fluoro2-nitrobenzene (13.3 g) in acetic acid (100 ml) and ethyl acetate (70 ml) was dropwise added thereto, and the resultant mixture was refluxed at 80° C. for 2 hours. The reaction mixture was filtered by celite. The filtrate was extracted with ethyl acetate, and the extract was neutralized with a saturated sodium hydrogen carbonate solution. The organic layer was washed with water, dried and concentrated under reduced pressure to give 7.0 g of 4-(N-acetylamino)-2-amino-1-chloro-5-fluorobenzene. M.P., 140.5°-141.5° C.
Workup
- filtrationThe reaction mixture was filtered by celite
- extractionThe filtrate was extracted with ethyl acetate
- washThe organic layer was washed with water
- customdried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-63bd24530f764cb6abc029b773f7a2e1
- Source dataset
- uspto-grants-1987_11
- Patent number
- US04709049
Reaction notes
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