Dimethyl malonate → HCID 67010726, compound

HRID 2194513Notes

Reaction equation

HRID 2194513 reaction equation
[CH3:1][NH:2][C:3]1[N:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:11](OC)(=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14].N1CCCCC1>CO>[CH3:1][N:2]1[C:3]2[C:4](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:11]1=[O:17]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 8082PiperidineHCID 31493522-(methylamino)nicotinaldehyde

Product 1

HCID 67010726HCID 67010726, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

8.66 g (64.5 mmol) of 2-(methylamino)nicotinaldehyde was dissolved in methanol (100 mL), and 12.68 g (96.0 mmol) of dimethyl malonate and 2.18 g (25.6 mmol) of piperidine were added to the solution. The resulting mixture was stirred for 7 hours at 80° C. The mixture was cooled, and a solid precipitated therefrom was separated by filtration. The solid was washed with diisopropyl ether, and thus 11.71 g (yield: 84%) of the title compound was obtained as a pale yellow solid.

Workup

  1. temperatureThe mixture was cooled
  2. customa solid precipitated
  3. customtherefrom was separated by filtration
  4. washThe solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-6357afab588b43b4a23c8db92b345db0
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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