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

HRID 636540Notes

Reaction equation

HRID 636540 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][CH2:15][CH2:14][C:13]=2[NH:12][C:11]([CH3:20])=[C:10]1[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22]>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][CH2:15][CH2:14][C:13]=2[N:12]=[C:11]([CH3:20])[C:10]=1[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22]

Participants

4

Reactant 1

HCID 2847040Propan-2-yl 4-(2,3-dichlorophenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

Product 1

HCID 9952423Isopropyl 4-(2,3-dichlorophenyl)-2-methyl-5-oxo-5,6,7,8-tetrahydroquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.5 g (3.8 mmol) of the compound from Example IV 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 is purified by MPLC (methylene chloride/ethyl acetate 10+1). After recrystallization, first from ether/petroleum ether and then from isopropanol/petroleum ether, 0.72 g (48% of theory) of the title compound is 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 is purified by MPLC (methylene chloride/ethyl acetate 10+1)
  5. customAfter recrystallization

Sources & evidence

ORD record
ord-f50c107cf108469ca7b2f466d895f2a1
Source dataset
uspto-grants-2001_02
Patent number
US06194428B1

Reaction notes

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