Diethyl (ethoxymethylene)malonate → diethyl N-(3-oxo-1-cyclohexen-1-yl)-aminomethylenemalonate

HRID 401233

Reaction equation

HRID 401233 reaction equation
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[CH:12][NH:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:18]

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 788923-Aminocyclohex-2-en-1-one

Product 1

HCID 12877078diethyl N-(3-oxo-1-cyclohexen-1-yl)-aminomethylenemalonateYield 90%

Conditions

Temperature
130 °C

Procedure

A mixture of 3-amino-cyclohex-2-enone (3.3 g, 29.7 mmol) and diethyl 2-(ethoxymethylene)malonate (6.7 g, 31.2 mmol) was stirred at 130° C. for 4 h. The reaction mixture was concentrated under reduced pressure and the resulting oil was purified by column chromatography (silica gel, ethyl acetate) to give 2-[(3-oxo-cyclohex-1-enylamino)-methylene]-malonic acid diethyl ester (7.5 g, 90%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting oil was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-f834384df36a40938616eb219eee5085
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Linked notes

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