4-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene → 5-(methylsulfonyl)-2-[(1E)-prop-1-en-1-yl]aniline
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH3:13])=[C:7]([N+:14]([O-])=O)[CH:6]=1)(=[O:4])=[O:3]>CC(O)=O.[Fe]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH3:13])=[C:7]([CH:6]=1)[NH2:14])(=[O:3])=[O:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
A solution of 4-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene (Intermediate 59; 1.10 g; 4.56 mmol) in AcOH (7 ml) was treated with powdered iron (3.82 g; 68.4 mmol) and the reaction mixture was stirred at 90° C. for 25 min. Further AcOH was added (20 mL), the solid was filtered off and rinsed with EtOAc. The solvents were removed under reduced pressure, the residue was taken up in EtOAc and washed with saturated NaHCO3 solution twice the with brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give the title compound as a brown oil (784 mg, 81%).
Workup
- filtrationthe solid was filtered off
- washrinsed with EtOAc
- customThe solvents were removed under reduced pressure
- washwashed with saturated NaHCO3 solution twice the with brine
- customThe organic phase was dried on MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-55328cad460c4d87b5cd0170de8399c1
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273769B2
Reaction notes
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