1,3-Diethyl 2-oxopropanedioate → Ethyl 2-oxo-1-(2-propynyl)-1,2-dihydroquinoxaline-3-carboxylate

HRID 240345Notes

Reaction equation

HRID 240345 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])[C:2]#[CH:3].O=[C:13]([C:19]([O:21]CC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1>[O:21]=[C:19]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:11][C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:4]1[CH2:1][C:2]#[CH:3]

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 15420533N-(2-propynyl) 1,2-phenylenediamine

Product 1

HCID 86643865Ethyl 2-oxo-1-(2-propynyl)-1,2-dihydroquinoxaline-3-carboxylateYield 93.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.2 g (62.9 mmol) of N-(2-propynyl) 1,2-phenylenediamine and 12.1 g (69.2 mmol) of diethyl ketomalonate were dissolved in toluene (100 mL), and the solution was refluxed for 3 hours. After confirming the completion of the reaction, the reaction solution was concentrated under reduced pressure, and the solid matter thus obtained was washed with diisopropyl ether, to obtain 15.0 g (yield: 93%) of ethyl 2-oxo-1-(2-propynyl)-1,2-dihydroquinoxaline-3-carboxylate as a white powder.

Workup

  1. temperaturethe solution was refluxed for 3 hours
  2. customthe completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customthe solid matter thus obtained
  5. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-dad029e8f2bc4ceaaefeb22130989886
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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