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

HRID 2058865Notes

Reaction equation

HRID 2058865 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH2:9][C:10](=[O:16])[CH2:11][C:12](=[O:15])[CH2:13][CH3:14])[CH:6]=[CH:7][CH:8]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>>[CH3:21][N:22]1[CH:24]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:17])([F:18])[F:1])[CH:4]=2)[C:10](=[O:16])[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[CH:23]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 132018041-[3-(Trifluoromethyl)phenyl]hexane-2,4-dione

Product 1

HCID 1578584(1H)-Pyridinone, 1-methyl-3-(1-oxopropyl)-5-[3-(trifluoromethyl)phenyl]-

Procedure

A 29.1 g. portion of 1-(3-trifluoromethylphenyl)-2,4-hexanedione was combined with 120 ml. of N,N-dimethylformamide dimethyl acetal and the mixture was stirred under reflux overnight. The mixture was then evaporated to a thick dark brown oil under vacuum, and the residue was dissolved in 250 ml. of methanol. Forty g. of methylamine hydrochloride was added and the mixture was stirred under reflux for 2 hours, and at ambient temperature for 60 hours. The mixture was then evaporated under vacuum to dryness, and the residue was taken up in water and diethyl ether. The organic layer was dried over magnesium sulfate and evaporated under dryness to a dark brown solid, which was chromatographed on a 500 g. silica gel column with ethyl acetate as the eluting solvent. The product-containing fractions were combined and evaporated under vacuum to obtain a light orange solid, which was crystallized from diisopropyl ether to obtain 3.04 g. of the desired product, m.p. 136°-138°. Nmr analysis in DMSOd6 showed peaks at δ7.6-8.3 (m, 6H, aromatic); 3.8 (s, 3H, N--CH3); 2.9-3.3 (q, 2H, COCH2CH3); 0.9-1.1 (t, 3H, COCH2CH3).

Workup

  1. temperatureunder reflux overnight
  2. customThe mixture was then evaporated to a thick dark brown oil under vacuum
  3. dissolutionthe residue was dissolved in 250 ml
  4. additionof methylamine hydrochloride was added
  5. temperatureunder reflux for 2 hours
  6. customThe mixture was then evaporated under vacuum to dryness
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. customevaporated under dryness to a dark brown solid, which
  9. customwas chromatographed on a 500 g
  10. customevaporated under vacuum
  11. customto obtain a light orange solid, which
  12. customwas crystallized from diisopropyl ether
  13. customto obtain 3.04 g

Sources & evidence

ORD record
ord-e8b2e9de66c04a8894a079e748057cfb
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

Loading…