2-(3-Fluoro-4-nitrobenzamido)acetic acid → 2-(4-Amino-3-fluorobenzamido)acetic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6]>CC(O)=O.CCOC(C)=O.[Fe]>[NH2:15][C:14]1[CH:13]=[CH:12][C:4]([C:5]([NH:7][CH2:8][C:9]([OH:11])=[O:10])=[O:6])=[CH:3][C:2]=1[F:1]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 87.5 °C
Procedure
To a suspension of iron powder (231 mg, 4.13 mmol) in AcOH (2 mL) was added 2-(3-fluoro-4-nitrobenzamido)acetic acid (100 mg, 0.413 mmol) at rt and stirred at 85-90° C. for 15 min. The reaction mixture was attained to rt and diluted with EtOAc (20 mL). The solution was stirred for 5 min and filtered through celite. The celite bed was washed with EtOAc (10 mL) and the combined organic layer was evaporated under reduced pressure. The residue was chromatographed over silica gel column using chloroform:methanol (70:30) as eluents to give the product as an off-white color solid (62 mg, 71%), 198-200° C.
Workup
- customwas attained to rt
- stirringThe solution was stirred for 5 min
- filtrationfiltered through celite
- washThe celite bed was washed with EtOAc (10 mL)
- customthe combined organic layer was evaporated under reduced pressure
- customThe residue was chromatographed over silica gel column
Sources & evidence
- ORD record
- ord-b243069e5cc0469dbbf7a5c0767c2291
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906344B2
Reaction notes
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