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

HRID 1707096Notes

Reaction equation

HRID 1707096 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-0c27cc91aeae42459c2c4ac48a5c826c
Source dataset
uspto-grants-1980_06
Patent number
US04209626

Reaction notes

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