Water → 3,4-dihydro-5-(4-acetonylphenyl)-6-methyl-2(1H)-pyridone

HRID 465453Notes

Reaction equation

HRID 465453 reaction equation
S(=O)(=O)(O)O.C1CO[C:8]([CH3:24])([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([C:21](=O)[CH3:22])[CH2:17][CH2:18][C:19]#[N:20])=[CH:12][CH:11]=2)[O:7]1.[OH2:27]>C(O)(=O)C>[CH2:9]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]=2[CH3:22])=[CH:12][CH:11]=1)[C:8]([CH3:24])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 198745084-(4-(2,2-(Ethylenedioxy)propyl)phenyl)-5-oxo-hexane nitrile

Product 1

HCID 198745593,4-dihydro-5-(4-acetonylphenyl)-6-methyl-2(1H)-pyridone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated sulphuric acid (5 ml) was added dropwise to a solution of 4-(4-(2,2-(ethylenedioxy)propyl)phenyl)-5-oxo-hexane nitrile (3.09 g) in glacial acetic acid (21 ml). The orange solution was allowed to stand at room temperature for 3 days then poured into water and allowed to stand for 2 hr. The solution was extracted with chloroform, the organic layer separated, washed with sodium bicarbonate solution, dried (MgSO4) and evaporated to an oil (2.44 g) which was chromatographed on silica. Elution with chloroform gave 3,4-dihydro-5-(4-acetonylphenyl)-6-methyl-2(1H)-pyridone as an oil.

Workup

  1. waitto stand for 2 hr
  2. extractionThe solution was extracted with chloroform
  3. customthe organic layer separated
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customevaporated to an oil (2.44 g) which
  7. customwas chromatographed on silica
  8. washElution with chloroform

Sources & evidence

ORD record
ord-7d261a97cc6a449e9da15e230b0d5ba5
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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