N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinoline → N-ethoxalyl-2-ethoxycarbonylethyltetrahydroquinoline

HRID 52490Notes

Reaction equation

HRID 52490 reaction equation
[C:1]([N:8]1[C:17]2[CH:12]([CH2:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH:9]1[CH:18]=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[H][H]>C(O)C.[Pd]>[C:1]([N:8]1[C:17]2[CH:12]([CH2:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH:9]1[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

5

Reactant 2

HCID 67722040N-ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 67721858N-ethoxalyl-2-ethoxycarbonylethyltetrahydroquinolineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-Ethoxalyl-2-ethoxycarbonylethenyltetrahydroquinoline (4 g, 12.1 mmol) in ethanol (100 mL) was hydrogenated over 10% palladium on carbon (500 mL) under atmospheric pressure of hydrogen for 1.5 h at room temperature. The mixture was filtered through celite and the filtrate was concentrated to give 3.83 g of N-ethoxalyl-2-ethoxycarbonylethyltetrahydroquinoline (95%): 1H NMR (270 MHz, CDCl3) δ7.03~7.19 (m, 4H), 4.78 (m, 1H), 4.11(q, 4H, J 7 Hz), 2.73 (t, 2H, J=6 Hz), 2.47 (m, 1H), 1.69 (m, 1H), 1.25 (t, 3H, J=7 Hz), 1.11 (t, 3H, J=7Hz).

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7587a164b53b4fe89c612e955bd90768
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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