Dimethylformamide dimethyl acetal → 4(1H)-Pyridinone, 1-methyl-3-(1-oxobutyl)-5-[3-(trifluoromethyl)phenyl]-

HRID 2058867Notes

Reaction equation

HRID 2058867 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH2:9][C:10](=[O:17])[CH2:11][C:12](=[O:16])[CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][CH:8]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24].Cl.CN>CO>[C:12]([C:11]1[C:10](=[O:17])[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:18])([F:19])[F:1])[CH:4]=2)=[CH:24][N:23]([CH3:25])[CH:22]=1)(=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 6364545Methylamine hydrochlorideHCID 132018051-[3-(Trifluoromethyl)phenyl]heptane-2,4-dione

Product 1

HCID 1578594(1H)-Pyridinone, 1-methyl-3-(1-oxobutyl)-5-[3-(trifluoromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.6 g. of 1-(3-trifluoromethylphenyl)-2,4-heptanedione and 50 ml. of N,N-dimethylformamide dimethyl acetal was stirred for 3 hours at reflux temperature, and then at ambient temperature overnight. The mixture was evaporated under vacuum to obtain 2.3 g. of a thick dark oil, which was dissolved in 25 ml. of methanol. Five g. of methylamine hydrochloride was added, and the mixture was stirred under reflux for 2 hours and then at ambient temperature overnight. The mixture was then evaporated under vacuum, and the residue was partitioned between diethyl ether and water. The organic layer was dried over magnesium sulfate and evaporated under vacuum to obtain a thick brown oil, which was chromatographed on a 300 g. silica gel column with 2:3 ethyl acetate:dichloromethane. The product-containing fractions were combined, and the product crystallized from the solvent on standing. The product was collected and triturated under hexane to obtain 0.19 g. of the desired product, m.p. 93°-94°. Nmr analysis in DMSOd6 showed peaks at δ7.6-8.3 (m, 6H, aromatic); 3.9 (s, 3H, N--CH3); 3.0-3.2 (t, 2H, COCH2); 1.3-1.9 (m, 2H, CH2CH3); 0.8-1.1 (t, 3H, CH2CH3).

Workup

  1. additionA mixture of 1.6 g
  2. temperatureat reflux temperature
  3. customat ambient temperature
  4. customovernight
  5. customThe mixture was evaporated under vacuum
  6. customto obtain 2.3 g
  7. dissolutionof a thick dark oil, which was dissolved in 25 ml
  8. temperatureunder reflux for 2 hours
  9. customat ambient temperature
  10. customovernight
  11. customThe mixture was then evaporated under vacuum
  12. customthe residue was partitioned between diethyl ether and water
  13. dry with materialThe organic layer was dried over magnesium sulfate
  14. customevaporated under vacuum
  15. customto obtain a thick brown oil, which
  16. customwas chromatographed on a 300 g
  17. customthe product crystallized from the solvent on standing
  18. customThe product was collected
  19. customtriturated under hexane
  20. customto obtain 0.19 g

Sources & evidence

ORD record
ord-8928ecde6c63445daaef88369e6aa675
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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