Methyl 4-chloro-3-nitrobenzoate → Methyl 3-Amino-4-chlorobenzoate
Reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-])=O>C(O)(=O)C.C(=O)(O)[O-].[Na+].[Fe]>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[Cl:1])[C:6]([O:8][CH3:9])=[O:7]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 20 °C
Procedure
A solution of methyl 4-chloro-3-nitrobenzoate (10 g) dissolved in acetic acid (100 mL) was treated with Iron powder (10.36 g) under nitrogen. The resulting mixture was stirred vigorously at 20° C. for 2 h. The reaction mixture was filtered through celite and the filtrate evaporated to dryness to afford crude product. The residue was diluted with aqueous sodium bicarbonate solution (200 mL), and extracted with dichloromethane (250 mL). The organic layer was separated, dried (MgSO4), filtered and evaporated to afford the sub title compound (8.41 g).
Workup
- filtrationThe reaction mixture was filtered through celite
- customthe filtrate evaporated to dryness
- customto afford crude product
- extractionextracted with dichloromethane (250 mL)
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-dbc2edf8677b4f2a8d5834eec70c788a
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163905B2
Reaction notes
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