Diethyl (ethoxymethylene)malonate → Diethyl 2-([[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]methylene)malonate

HRID 497934

Reaction equation

HRID 497934 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[CH:21]=[C:20]([NH2:22])[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[N:18]=1>>[CH3:16][C:17]1[CH:21]=[C:20]([NH:22][CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[N:18]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7351323-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 22320362Diethyl 2-([[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]methylene)malonateYield 96%

Conditions

Temperature
120 °C

Procedure

A mixture of diethyl ethoxymethylenemalonate (32.5 g, 0.15 mol) and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-amine (23.8 g, 0.137 mol) was heated under reflux at 120° C. for 1 hour. After the mixture was allowed to cool to room temperature, the reaction solvent was evaporated under reduced pressure. The crude crystals thus obtained were filtered and washed with diethylether to give the title compound (45 g, 96% yield).

Workup

  1. temperaturewas heated
  2. temperatureto cool to room temperature
  3. customthe reaction solvent was evaporated under reduced pressure
  4. customThe crude crystals thus obtained
  5. filtrationwere filtered
  6. washwashed with diethylether

Sources & evidence

ORD record
ord-34b8fc18d8c74f8bba3d7ab89fdd719a
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Linked notes

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