Dimethyl malonate → Methyl 1,2-dihydro-2-oxo-5-[3-(trifluoromethyl)phenyl]-3-pyridinecarboxylate

HRID 1733581Notes

Reaction equation

HRID 1733581 reaction equation
C[O-].[Na+].[C:4]([O:11][CH3:12])(=[O:10])[CH2:5][C:6]([O:8]C)=O.[NH2:13][CH:14]=[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)[CH:16]=O>CO>[O:8]=[C:6]1[C:5]([C:4]([O:11][CH3:12])=[O:10])=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=2)=[CH:14][NH:13]1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 10942334Sodium MethoxideHCID 867370753-Amino-2-[3-(trifluoromethyl)phenyl]-2-propenal

Product 1

HCID 10357255Methyl 1,2-dihydro-2-oxo-5-[3-(trifluoromethyl)phenyl]-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.5 g. of sodium methoxide in 85 ml. of methanol is added 2.25 g. of dimethyl malonate and 2.93 g. of 3-amino-2-[3-(trifluoromethyl)phenyl]-2-propenal. The mixture is stirred at room temperature for 16 hours with precipitation of a yellow solid. The mixture is heated at reflux temperature for 2 hours, cooled and filtered to obtain a white solid. The solid is washed with ether, suspended in water and acidified with hydrochloric acid to yield 1.75 g. of the product of the Example as a white solid, m.p. 195°-201° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature for 2 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customto obtain a white solid
  6. washThe solid is washed with ether
  7. customto yield 1.75 g

Sources & evidence

ORD record
ord-8340ada5813f4eeaa65ed4da7d4d16fe
Source dataset
uspto-grants-1980_12
Patent number
US04242515

Reaction notes

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