Dimethylformamide dimethyl acetal → 3-Acetyl-5-(3-bromophenyl)-1-methylpyridin-4(1H)-one

HRID 2058863Notes

Reaction equation

HRID 2058863 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[C:11]([C:10]1[C:9](=[O:14])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[CH:19][N:18]([CH3:20])[CH:17]=1)(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 132018071-(3-Bromophenyl)pentane-2,4-dione

Product 1

HCID 132018123-Acetyl-5-(3-bromophenyl)-1-methylpyridin-4(1H)-one

Procedure

To 1.5 g. of 1-(3-bromophenyl)-2,4-pentanedione was added 25 ml. of N,N-dimethylformamide dimethyl acetal. The mixture was stirred at reflux temperature for 18 hours, cooled and evaporated to a thick oil under vacuum. The oil was dissolved in 500 ml. of tetrahydrofuran, and 10 ml. of 40% aqueous methylamine was added. The mixture was stirred at ambient temperature for 4 hours, and was then evaporated under vacuum. The residue was dissolved in 800 ml. of dichloromethane, and washed with 500 ml. of water. The organic layer was dried over magnesium sulfate, treated with activated charcoal, filtered and evaporated under vacuum. The solids were recrystallized twice from dichloromethane/diisopropyl ether. The solids were then chromatographed on a silica gel column with ethyl acetate as the eluting solvent. The yield was 0.8 g. of the desired product, m.p. 192°-194°. Nmr analysis in DMSOd6 showed peaks at δ7.25-8.40 (m, 6H, aromatic); 3.75 (s, 3H, N--CH3); 2.53 (s, 3H, COCH3).

Workup

  1. temperatureat reflux temperature for 18 hours
  2. temperaturecooled
  3. customevaporated to a thick oil under vacuum
  4. dissolutionThe oil was dissolved in 500 ml
  5. additionof 40% aqueous methylamine was added
  6. stirringThe mixture was stirred at ambient temperature for 4 hours
  7. customwas then evaporated under vacuum
  8. dissolutionThe residue was dissolved in 800 ml
  9. washof dichloromethane, and washed with 500 ml
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. additiontreated with activated charcoal
  12. filtrationfiltered
  13. customevaporated under vacuum
  14. customThe solids were recrystallized twice from dichloromethane/diisopropyl ether
  15. customThe solids were then chromatographed on a silica gel column with ethyl acetate as the eluting solvent

Sources & evidence

ORD record
ord-b4969cf9326243579be2fa4d82b48ac6
Source dataset
uspto-grants-1982_03
Patent number
US04319916

Reaction notes

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