Hydrazine → HCID 22353179, compound

HRID 895355Notes

Reaction equation

HRID 895355 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6](=O)[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)C.[NH2:21][NH2:22]>C(#N)C>[CH3:18][O:17][C:9]1[CH:8]=[C:7]([C:6]2[CH2:5][C:4](=[O:3])[NH:21][N:22]=2)[CH:12]=[C:11]([O:13][CH3:14])[C:10]=1[O:15][CH3:16]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 76443Ethyl 3-oxo-3-(3,4,5-trimethoxyphenyl)propionate

Product 1

HCID 22353179HCID 22353179, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 3-oxo-3-(3,4,5-trimethoxyphenyl)-propionic acid ethyl ester (2.82 g, 10 mmol) in dry acetonitrile (15 mL) was added to anhydrous hydrazine (640 mL, 20 mmol) at room temperature. After 1 hour, the mixture was heated to reflux for 16 hours. The mixture was diluted with acetonitrile (20 mL) and the solid was filtered. The solid was washed with acetonitrile (10 mL) and dried under nitrogen to afford 2.2 g of title compound (k). Preparation of 4-Dimethylaminomethylene-5-(3,4,5-Trimethoxyphenyl)-2,4-Dihydro-Pyrazol-3-one (1):

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 hours
  3. filtrationthe solid was filtered
  4. washThe solid was washed with acetonitrile (10 mL)
  5. customdried under nitrogen

Sources & evidence

ORD record
ord-8c9b2d685ca14f66a6271a5bb6a2c8a9
Source dataset
uspto-grants-2005_07
Patent number
US06916798B2

Reaction notes

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