Benzoylacetone → HCID 178422627, compound

HRID 1471934Notes

Reaction equation

HRID 1471934 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:14][NH2:15]>C(O)C>[CH3:10][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:15][N:14]=1

Participants

4

Reactant 2

HCID 7166BenzoylacetoneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 178422627HCID 178422627, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-phenylbutane-1,3-dione (5.0 g, 30.8 mmol) in ethanol (50 mL), was added hydrazine hydrate (1.54 g, 30.8 mmol) at ambient temperature. The reaction was refluxed for 5 h. After cooling, the reaction was concentrated under reduced pressure and extracted with ethyl acetate. The extract was dried over MgSO4 and concentrated under reduced pressure. The residue was added 10% ethyl acetate in hexane. The precipitate was filtered and washed with hexane. The white solid was dried in air to give the title compound (3.9 g). LCMS m/z=159.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 3H), 6.65 (s, 1H), 7.34 (m, 1H), 7.42 (m, 2H), 7.82 (m, 2H).

Workup

  1. temperatureThe reaction was refluxed for 5 h
  2. temperatureAfter cooling
  3. concentrationthe reaction was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was added 10% ethyl acetate in hexane
  8. filtrationThe precipitate was filtered
  9. washwashed with hexane
  10. customThe white solid was dried in air

Sources & evidence

ORD record
ord-0d528e6a1e944e87abc3b245fb4b3619
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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