Propan-2-yl 4-(2,3-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate → Isopropyl 4-(2,3-dichlorophenyl)-2,7,7-trimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate

HRID 636541Notes

Reaction equation

HRID 636541 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:18]2[C:17](=[O:19])[CH2:16][C:15]([CH3:21])([CH3:20])[CH2:14][C:13]=2[NH:12][C:11]([CH3:22])=[C:10]1[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[C:18]2[C:17](=[O:19])[CH2:16][C:15]([CH3:20])([CH3:21])[CH2:14][C:13]=2[N:12]=[C:11]([CH3:22])[C:10]=1[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]

Participants

4

Reactant 1

HCID 2847332Propan-2-yl 4-(2,3-dichlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Product 1

HCID 21255222Isopropyl 4-(2,3-dichlorophenyl)-2,7,7-trimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.6 g (3.8 mmol) of the compound from Example V are dissolved in 350 ml of CH2Cl2 and treated with 7.5 g of MnO2. The mixture is kept under reflux for 2 h, solid is filtered off with suction through Celite and the filtrate is concentrated. The residue crystallizes from ether/petroleum ether. 1.1 g (69% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationsolid is filtered off with suction through Celite
  3. concentrationthe filtrate is concentrated
  4. customThe residue crystallizes from ether/petroleum ether

Sources & evidence

ORD record
ord-197523b48de04bfd9a8fe1af2b3933b4
Source dataset
uspto-grants-2001_02
Patent number
US06194428B1

Reaction notes

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