1,3-Diethyl 2-oxopropanedioate → Ethyl 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

HRID 1942158Notes

Reaction equation

HRID 1942158 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([NH:11][C:12]3[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:9]=[CH:10][C:2]1=2.O=[C:20]([C:26](OCC)=[O:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([N:11]3[C:12]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:18]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:26]3=[O:27])[CH:9]=[CH:10][C:2]1=2

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 43148731N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzene-1,2-diamine

Product 1

HCID 67533036Ethyl 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.0 g (21 mmol) of N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzene-1,2-diamine and 3.9 g (22 mmol) of diethyl ketomalonate were dissolved in toluene (60 ml), and the solution was heated to reflux for 12 hours while removing water using a Dean-Stark apparatus. The reaction solution was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=2:3) to obtain 4.6 g (yield: 63%) of ethyl 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as a milky yellow powder.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 12 hours
  3. customwhile removing water using a Dean-Stark apparatus
  4. washThe reaction solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel chromatography (developing solvent: ethyl acetate:hexane=2:3)

Sources & evidence

ORD record
ord-f1e0742e619d45bcb131881949db4408
Source dataset
uspto-grants-2013_03
Patent number
US08389523B2

Reaction notes

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