Ethyl 2-methyl-6-nitrobenzoate → Ethyl 2-amino-6-methylbenzoate
Reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([N+:13]([O-])=O)[CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.C(O)C.O.[Fe]>[NH2:13][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Procedure
A reaction mixture of 185 g of ethyl 6-methyl-2-nitrobenzoate and 176 g of powdered iron in 343 mL of glacial acetic acid and 2200 mL of ethanol was heated at reflux for 5 hours. The reaction mixture was allowed to cool, diluted with excess water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated to an orange oil 148.3 g.
Workup
- temperaturewas heated
- temperatureat reflux for 5 hours
- temperatureto cool
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated to an orange oil 148.3 g
Sources & evidence
- ORD record
- ord-30b7f14ea9e4410f82ab57807a24ad3a
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04927453
Reaction notes
Loading…