Diethyl (ethoxymethylene)malonate → Diethyl [[(6-methyl-2-pyridyl)amino]methylene]malonate

HRID 2378101Notes

Reaction equation

HRID 2378101 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[CH3:16][C:17]1[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[CH2:14]([O:13][C:11](=[O:12])[C:5](=[CH:4][NH:23][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:16])[N:22]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:15]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 157652-Amino-6-methylpyridine

Product 1

HCID 83264Diethyl [[(6-methyl-2-pyridyl)amino]methylene]malonateYield 106.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add diethyl ethoxymethylenemalonate (10.0 ml, 55.0 mmol) to a solution of 6-methyl-pyridin-2-ylamine (5.41 g, 50.0 mmol) in toluene (100 ml). Heat the mixture under reflux overnight. Evaporate the solvent in vacuo to provide 2-[(6-methyl-pyridin-2-ylamino)-methylene]-malonic acid diethyl ester (14.8 g) as a white solid. MS (ES+): 279 (M+H).

Workup

  1. temperatureHeat the mixture
  2. temperatureunder reflux overnight
  3. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-72c4d722c478427eb8c94cc1e20851bb
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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