Malonamide → 1,2-Dihydro-2-oxo-5-[3-(trifluoromethyl)phenyl]-3-pyridinecarboxamide

HRID 1733578Notes

Reaction equation

HRID 1733578 reaction equation
[C:1]([NH2:7])(=[O:6])[CH2:2][C:3]([NH2:5])=[O:4].C[O-].[Na+].CN(C)[CH:13]=[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[CH:15]=O>CO>[O:4]=[C:3]1[C:2]([C:1]([NH2:7])=[O:6])=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:26])[F:25])[CH:18]=2)=[CH:13][NH:5]1

Participants

5

Reactant 3

HCID 7911MalonamideHCID 37090863-(Dimethylamino)-2-[3-(trifluoromethyl)phenyl]prop-2-enalHCID 10942334Sodium Methoxide

Product 1

HCID 104689641,2-Dihydro-2-oxo-5-[3-(trifluoromethyl)phenyl]-3-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.1 g. of malonamide and 1.1 g. of sodium methoxide in 50 ml. of methanol is added 2.43 g. of 3-(dimethylamino)-2-[3-(trifluoromethyl)phenyl]-2-propenal. The resulting mixture is heated at reflux temperature for 12 hours. The mixture is cooled, concentrated and acidified with hydrochloric acid to yield 800 mg. of the product of the Example as a yellow solid m.p. 276.5°-278.5° C.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux temperature for 12 hours
  3. temperatureThe mixture is cooled
  4. concentrationconcentrated
  5. customto yield 800 mg

Sources & evidence

ORD record
ord-9eb5940c5c3643b8a0fb95fd9a60ac47
Source dataset
uspto-grants-1980_12
Patent number
US04242515

Reaction notes

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