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

HRID 557158

Reaction equation

HRID 557158 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-0d57e62ac2eb46a29aa32971c575f11e
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Linked notes

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