Hydrazine hydrate (1:1) → N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-5-oxopyrazolidine-3-carboxamide

HRID 1641451Notes

Reaction equation

HRID 1641451 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:19])/[CH:13]=[CH:14]\[C:15](OC)=[O:16])=[C:7]([C:20](=[O:27])[NH:21][CH:22]([CH:24]2[CH2:26][CH2:25]2)[CH3:23])[CH:6]=1>C(O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:13]2[CH2:14][C:15](=[O:16])[NH:3][NH:2]2)=[O:19])=[C:7]([C:20](=[O:27])[NH:21][CH:22]([CH:24]2[CH2:26][CH2:25]2)[CH3:23])[CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66737717Methyl 4-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylamino)-4-oxoisocrotonate

Product 1

HCID 44185604N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-5-oxopyrazolidine-3-carboxamideYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.58 g of hydrazine monohydrate was dropwise added to a mixed liquid comprising 25 g of methyl 4-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylamino)-4-oxoisocrotonate and 250 ml of ethanol, followed by reflux with heating. After stirring for 5.5 hours, the reaction liquid was stood to cool. The precipitated crystals were subjected to suction filtration. The crystals collected after the filtration were washed with ethyl acetate and then with hexane and air dried to obtain 13 g of the desired product.

Workup

  1. temperatureby reflux
  2. temperaturewith heating
  3. customthe reaction liquid
  4. temperatureto cool
  5. filtrationThe precipitated crystals were subjected to suction filtration
  6. customThe crystals collected
  7. filtrationafter the filtration
  8. washwere washed with ethyl acetate
  9. dry with materialwith hexane and air dried

Sources & evidence

ORD record
ord-32985c6815b94f4b9c062ea26e2d8738
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

Loading…