Propyl Acetate → Ethyl 5-(4-fluorophenyl)-1-isopropyl-4-oxo-1,4-dihydropyridine-3-carboxylate

HRID 1428081Notes

Reaction equation

HRID 1428081 reaction equation
CO[CH:3](OC)[N:4](C)[CH3:5].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12][CH:11]=1.C(O[CH2:29][CH2:30][CH3:31])(=O)C>>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:17](=[O:24])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:3][N:4]([CH:30]([CH3:31])[CH3:29])[CH:5]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 7997Propyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 10585213Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

Product 1

HCID 89861067Ethyl 5-(4-fluorophenyl)-1-isopropyl-4-oxo-1,4-dihydropyridine-3-carboxylate

Conditions

Temperature
90 °C

Procedure

N,N-Dimethylformamide dimethylacetal (3.6 ml) was added to a solution of ethyl 4-(4-fluorophenyl)-3-oxobutanoate (1200 mg) in n-propyl acetate (13 ml) at room temperature, and the mixture was stirred at 90° C. for four hours. The solvent was distilled off under reduced pressure, and ethanol (18 ml) was added, followed by addition of 2-propylamine (688 μl). After stirring at 60° C. for one hour, 2-propylamine (459 μl) was added and the mixture was further stirred at 60° C. for one hour. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->80:1 (v/v)] to give 620 mg of the title compound as an oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and ethanol (18 ml)
  2. additionwas added
  3. additionfollowed by addition of 2-propylamine (688 μl)
  4. stirringAfter stirring at 60° C. for one hour
  5. addition2-propylamine (459 μl) was added
  6. stirringthe mixture was further stirred at 60° C. for one hour
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->80:1 (v/v)]

Sources & evidence

ORD record
ord-09143ca151c94ccdbe4db37e5b006437
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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