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

HRID 448822Notes

Reaction equation

HRID 448822 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 44185603Methyl 4-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylamino)-4-oxocrotonate

Product 1

HCID 44185604N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-5-oxopyrazolidine-3-carboxamideYield 28.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixed liquid of 90 mg of hydrazine monohydrate and 3 ml of ethanol, was added to a mixed liquid of 0.56 g of methyl 4-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylamino)-4-oxocrotonate and 3 ml of ethanol, followed by rinsing with 2 ml of ethanol and then by heating and refluxing for 6 hours. The reaction liquid was left to cool, and then, the precipitated crystals were collected by suction filtration, and the crystals were washed with ethanol and air-dried to obtain 0.16 g of the desired product (melting point: 248° C.).

Workup

  1. washby rinsing with 2 ml of ethanol
  2. temperatureby heating
  3. temperaturerefluxing for 6 hours
  4. customThe reaction liquid
  5. waitwas left
  6. temperatureto cool
  7. filtrationthe precipitated crystals were collected by suction filtration
  8. washthe crystals were washed with ethanol
  9. customair-dried

Sources & evidence

ORD record
ord-eab9d7c590c74bc38e37f863b92a7445
Source dataset
uspto-grants-2013_07
Patent number
US08481744B2

Reaction notes

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