1,2,3,4-Tetrahydroquinoline → ethyl 3-(3,4-dihydroquinolin-1(2H)-yl)-2-oxopropanoate

HRID 910060

Reaction equation

HRID 910060 reaction equation
[C:1]([O:6][CH2:7][CH2:8]Br)(=[O:5])[C:2]([CH3:4])=[O:3].[NH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH2:7]([O:6][C:1](=[O:5])[C:2](=[O:3])[CH2:4][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)[CH3:8]

Participants

4

Reactant 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 86587973Bromoethyl pyruvate

Product 1

HCID 20729419ethyl 3-(3,4-dihydroquinolin-1(2H)-yl)-2-oxopropanoateYield 111.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add bromoethyl pyruvate (40 mL, 0.29 mol) to a solution of 1,2,3,4-tetrahydroquinoline (75.5 mL, 0.59 mol) in tetrahydrofuran (300 mL) dropwise over 30 minutes. Stir for 24 hours, filter the reaction mixture, rinse the filter cake well with tetrahydrofuran (100 mL), and concentrate the filtrate under reduced pressure to provide the desired compound as a red oil (79.7 g).

Workup

  1. filtrationfilter the reaction mixture
  2. washrinse the filter cake well with tetrahydrofuran (100 mL)
  3. concentrationconcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-bb50bfcab1d44a3ea0fedbc98d023025
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Linked notes

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