Hydrazine → HCID 67482515, compound

HRID 1817761Notes

Reaction equation

HRID 1817761 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=O)[CH2:14][C:15]([O:17]CC)=O)[CH:7]=[CH:6]2.[NH2:21][NH2:22]>CC(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[CH2:14][C:15](=[O:17])[NH:21][N:22]=1)[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 9321HydrazineHCID 3564017HCID 3564017, compound

Product 1

HCID 67482515HCID 67482515, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 3-(6-methoxy-2-naphthyl)-3-oxopropanoate (5.0 g, 18.3 mmol) and anhydrous hydrazine (0.63 ml 20 mmol) were refluxed in HOAc (100 ml) for 3 hours. Solvent was removed under reduced pressure, and the residue was washed with DCM and collected by filtration to give 5-(6-methoxy-2-naphthyl)-2,4-dihydro-3H-pyrazol-3-one as an off-white solid. This compound exists in the enol form in DMSO. NMR (500 MHz, DMSO-d6) δ: 3.87 (s, 3H); 5.95 (s, 1H); 7.17 (dd, J=2.7 Hz, 9.0 Hz, 1H); 7.31 (d, J=2.7 Hz, 1H); 7.74˜7.84 (m, 3H); 8.11 (br s, 1H); 9.66 (br s, 1H); 12 (br, 1H). MS C14H12N2O2 Cald: 240.09, Obsd: (M+1) 241.08.

Workup

  1. customSolvent was removed under reduced pressure
  2. washthe residue was washed with DCM
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e106baaad87b4f78af4781ef84643e80
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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