Malonamide → 2-Oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide

HRID 512458

Reaction equation

HRID 512458 reaction equation
[Na].C(O[CH:7]=[CH:8][C:9](=O)[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])CCC.[C:18]([NH2:24])(=[O:23])[CH2:19][C:20]([NH2:22])=[O:21]>C(O)C>[O:21]=[C:20]1[C:19]([C:18]([NH2:24])=[O:23])=[CH:7][CH:8]=[C:9]([C:10]([F:15])([F:16])[C:11]([F:12])([F:13])[F:14])[NH:22]1

Participants

5

Reactant 3

HCID 7911MalonamideHCID 5360545SodiumHCID 86624085HCID 86624085, compound

Product 1

HCID 598282382-Oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.22 g (9.7 mmol) of sodium was dissolved in 50 ml of ethanol, 2 g (8.1 mmol) of 1-butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one and 0.86 g (8.1 mmol) malonamide were added and the mixture was heated under reflux for 7 h. The mixture was concentrated, and 1N hydrochloric acid was added. The resulting precipitate was filtered off with suction and dried. This gave 1.9 g (94% of theory) of a yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 7 h
  3. concentrationThe mixture was concentrated
  4. addition1N hydrochloric acid was added
  5. filtrationThe resulting precipitate was filtered off with suction
  6. customdried

Sources & evidence

ORD record
ord-0e4cb7410b94483792ed6cf555936528
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Linked notes

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