Hydrazine hydrate (1:1) → HCID 178515601, compound

HRID 2182805Notes

Reaction equation

HRID 2182805 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](OCC)=[O:11])=[C:4]([F:16])[CH:3]=1.O.[NH2:18][NH2:19]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([OH:11])[NH:19][N:18]=2)=[C:4]([F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11195926Ethyl 3-(4-chloro-2-fluorophenyl)-3-oxopropanoate

Product 1

HCID 178515601HCID 178515601, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

428.4 g of ethyl 3-(4-chloro-2-fluorophenyl)-3-oxopropionate were initially charged in 1400 ml of ethanol. Over a period of 15 min, 92 g of hydrazine hydrate were added dropwise, the mixture was stirred at room temperature overnight, the precipitated solid was filtered off and the filtrate was concentrated to ⅓ of its original volume. The mixture was stirred for another two nights, the resulting solid was filtered off with suction and the filtrate was again concentrated to ⅓ of its original volume. This gave a total of 289.1 g (77.7%) of 3-(4-chloro-2-fluorophenyl)-5-hydroxy-1H-pyrazole as a colorless solid. M.p.: 194° C.

Workup

  1. filtrationthe precipitated solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. stirringThe mixture was stirred for another two nights
  4. filtrationthe resulting solid was filtered off with suction
  5. concentrationthe filtrate was again concentrated

Sources & evidence

ORD record
ord-bba5b1c3d3404caeb8cb53370bd9c065
Source dataset
uspto-grants-2005_05
Patent number
US06897322B2

Reaction notes

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