N-methyl-2-pyrrolidone → HCID 14304048, compound

HRID 2350973Notes

Reaction equation

HRID 2350973 reaction equation
CN1CCCC1=O.Br[C:9]1[C:14](=[O:15])[CH:13]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[F:34][C:35]([F:40])([F:39])C([O-])=O.[Na+]>O>[C:22]1([N:11]2[C:12]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:13][C:14](=[O:15])[C:9]([C:35]([F:40])([F:39])[F:34])=[C:10]2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 517019Sodium TrifluoroacetateHCID 14304035HCID 14304035, compound

Product 1

HCID 14304048HCID 14304048, compoundYield 20.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To 40 ml of 1-methyl-2-pyrrolidinone were added 2.0 g (0.0050 mole) of 3-bromo-1,2,6-triphenyl-4(1H)-pyridinone, 2.7 g (0.020 mole) of sodium trifluoroacetate and 1.9 g (0.010 mole) of cuprous iodide. The reaction mixture was then heated at 160° C. for 5 hours in a nitrogen atmosphere. After allowing the reaction mixture to cool down, it was poured into water, followed by extraction with ethyl ether. The organic layer (the extract) was washed with 50 ml of a saturated aqueous solution of sodium hydrogen carbonate. After washing the organic layer further with water, it was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off, and the residue was crystallized from a 1:3 mixed solvent of ethyl acetate and hexane to yield 0.4 g of 1,2,6-triphenyl-3-trifluoromethyl-4(1H)-pyridinone having a melting point of 222°-225° C.

Workup

  1. temperatureto cool down
  2. extractionfollowed by extraction with ethyl ether
  3. extractionThe organic layer (the extract)
  4. washwas washed with 50 ml of a saturated aqueous solution of sodium hydrogen carbonate
  5. washAfter washing the organic layer further with water, it
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customSubsequent to removal of the sodium sulfate
  8. distillationthe solvent was distilled off
  9. customthe residue was crystallized from a 1:3 mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-caad9234a4d14bf0a39b3a441549d6c4
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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