Methyl 2-chloro-3-nitrobenzoate → Methyl 3-amino-2-chlorobenzoate
Reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Ni]>[NH2:12][C:11]1[C:2]([Cl:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of methyl 2-chloro-3-nitrobenzoate (25 g, 116 mmol) in MeOH (150 mL) was added Raney Ni (3 g). The mixture was stirred under H2 atmosphere (50 psi at 25° C.) for 3.5 h. The catalyst was filtered, and the filtrate was concentrated under the reduced pressure to dryness to give the crude product, which was purified by recrystallization in EtOAc to afford the title compound (69 g, 83.5% yield, four batches combined). 1H NMR (400 MHz, CDCl3) δ ppm 6.70-7.25 (m, 3H), 4.40-4.50 (br, 2H), 3.87 (s, 3H).
Workup
- filtrationThe catalyst was filtered
- concentrationthe filtrate was concentrated under the reduced pressure to dryness
- customto give the crude product, which
- customwas purified by recrystallization in EtOAc
Sources & evidence
- ORD record
- ord-379e7475db30421e9a91bf8d2fd9afba
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09233956B2
Reaction notes
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