ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoate → HCID 67482987, compound

HRID 1817758Notes

Reaction equation

HRID 1817758 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:5]([CH2:7][C:8]([O:10]CC)=O)=O.[Cl-].[CH2:18]([O:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH:29]([NH2+:31][NH2:32])[CH3:30])=[CH:25][CH:24]=1)=[O:22])[CH3:19]>CC(O)=O>[Cl:16][C:14]1[CH:13]=[C:4]([C:5]2[CH2:7][C:8](=[O:10])[N:31]([CH:29]([C:26]3[CH:27]=[CH:28][C:23]([C:21]([O:20][CH2:18][CH3:19])=[O:22])=[CH:24][CH:25]=3)[CH3:30])[N:32]=2)[CH:3]=[C:2]([Cl:1])[CH:15]=1

Participants

4

Reactant 2

HCID 2758177ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoateHCID 86602021HCID 86602021, compound

Product 1

HCID 67482987HCID 67482987, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ethyl (3,5-dichlorobenzoyl)acetate (3.0 g, 11.5 mmol) and {1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinium chloride (2.55 g, 10.4 mmol) was refluxed in HOAc (80 ml) for 4 hr. The solvent was removed under reduced pressure, and the residue taken up with ethyl acetate, washed with sat. NaHCO3 2×, brine, and dried over Na2SO4. Flash column chromatography (SiO2, 0-5% ethyl acetate in DCM gradient) gave ethyl 4-{1-[3-(3,5-dichlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]ethyl}benzoate as a white solid. TLC (5% ethyl acetate-DCM) Rf 0.43. NMR (500 MHz, CDCl3) δ: 1.38 (t, J=7.1 Hz, 3H); 1.78 (d, J=7.0 Hz, 3H); 3.55 (d, J=22.6 Hz, 1H); 3.60 (d, J=22.6 Hz, 1H); 4.36 (q, J=7.1 Hz, 2H); 5.57 (q, J=7.0 Hz, 1H); 7.39 (t, J=1.9 Hz, 1H); 7.50 (d, J=8.4 Hz, 2H). 7.52 (d, J=1.9 Hz, 2H); 8.02 (d, J=8.4 Hz, 2H). MS C20H18Cl2N2O3 Cald: 404.07; Obsd (M+1): 405.20.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with sat. NaHCO3 2×, brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-3161d51e90dd471399465a733007e0f4
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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