ethyl (2E)-3-(4-chloro-2-nitrophenyl)prop-2-enoate → 7-Chloro-1,2,3,4-tetrahydroquinolin-2-one

HRID 910869Notes

Reaction equation

HRID 910869 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]=1

Participants

5

Reactant 1

HCID 10912128ethyl (2E)-3-(4-chloro-2-nitrophenyl)prop-2-enoate

Product 1

HCID 136907667-Chloro-1,2,3,4-tetrahydroquinolin-2-one

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

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

  1. customThe catalyst was removed by filtration through celite
  2. customthe filtrate was evaporated under reduced pressure to a brown solid, which
  3. customwas triturated with diethyl ether
  4. customto give a pink solid

Sources & evidence

ORD record
ord-52c70b9d5bec40fea6779a6494e1c3e0
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

Loading…