Ethyl Acetoacetate → HCID 57876142, compound

HRID 509694Notes

Reaction equation

HRID 509694 reaction equation
[CH2:1]([N:9]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)N)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:18]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:19][C:20]([CH3:22])=O>Cl>[CH3:22][C:20]1[N:9]([CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:11]2[C:16]([C:19]=1[C:18]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 578760211-(4-Methylphenyl)-1-(2-phenylethyl)hydrazine

Product 1

HCID 57876142HCID 57876142, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

1-phenethyl-1-p-tolylhydrazine (3.7 g, 16.3 mmol) was dissolved in ethanolic HCl (40 mL, pH of the solution was acidic) and ethyl acetoacetate (2.0 mL, 16.3 mmol) was added to it. The reaction mixture was heated at 110° C. for 1.5 h at which point the reaction was found complete by TLC and LC-MS. The reaction mixture was concentrated under reduced pressure, the residue was suspended in saturated aqueous NaHCO3 (pH 9) and extracted with ethyl acetate (100 mL×2). The organic layer was separated, dried (Na2SO4) and concentrated to obtain a crude product as dark brown oil. Purification of crude product by flash column chromatography (silica gel, 230-400 mesh, eluent: 5-10% ethyl acetate-hexanes) furnished 3.2 g of pure product as yellow solid.

Workup

  1. additionwas added to it
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate (100 mL×2)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto obtain a crude product as dark brown oil
  8. customPurification of crude product by flash column chromatography (silica gel, 230-400 mesh, eluent: 5-10% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-375933f28ab1421e9888f7623c97adc9
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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