ethyl (2E)-3-(4-chloro-2-nitrophenyl)prop-2-enoate → 7-Chloro-1,2,3,4-tetrahydroquinolin-2-one
Reaction equation
C([O:3][C:4](=O)/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[N+:14]([O-])=O)C>[Pt].Cl.C(OCC)(=O)C>[Cl:13][C:10]1[CH:9]=[C:8]2[C:7]([CH2:6][CH2:5][C:4](=[O:3])[NH:14]2)=[CH:12][CH:11]=1Participants
5
Procedure
A mixture of the product from step (i) (4.95 g) and 5% platinum on carbon (0.400 g) and a few drops of 2M hydrochloric acid in ethyl acetate (30 ml) was hydrogenated under a pressure of 3 bar. The catalyst was removed by filtration through celite and the filtrate was evaporated under reduced pressure to a brown solid, which was triturated with diethyl ether to give a pink solid. Yield 1.28 g
Workup
- customThe catalyst was removed by filtration through celite
- customthe filtrate was evaporated under reduced pressure to a brown solid, which
- customwas triturated with diethyl ether
- customto give a pink solid
Sources & evidence
- ORD record
- ord-52c70b9d5bec40fea6779a6494e1c3e0
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022248B2
Reaction notes
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