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

HRID 351569

Reaction equation

HRID 351569 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:11]([O:16][CH2:17][CH2:18]Br)(=[O:15])[C:12]([CH3:14])=[O:13]>O1CCCC1>[CH2:17]([O:16][C:11](=[O:15])[C:12](=[O:13])[CH2:14][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH3:18]

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

To a solution of 1,2,3,4-tetrahydroquinoline (75.5 mL, 0.59 mol) in tetrahydrofuran (300 mL) was added bromoethyl pyruvate (40 mL, 0.29 mol) dropwise over 30 minutes. Following 24 hours of stirring, the reaction mixture was filtered, the filter cake rinsed well with tetrahydrofuran (100 mL) and the filtrate concentrated under reduced pressure to dryness to give 79.7 g of the desired compound as a red oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe filter cake rinsed well with tetrahydrofuran (100 mL)
  3. concentrationthe filtrate concentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-56e7035677994545ac41a83b984eccb4
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Linked notes

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