Hydrazine hydrate (1:1) → 6-(p-Chloroacetylaminophenyl)-4,5-dihydropyridaz-3-one

HRID 354676Notes

Reaction equation

HRID 354676 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:18]=[CH:17][C:9]([C:10]([CH2:12][CH2:13][C:14](O)=[O:15])=O)=[CH:8][CH:7]=1)=[O:4].O.[NH2:20][NH2:21]>C(O)C>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:18]=[CH:17][C:9]([C:10]2[CH2:12][CH2:13][C:14](=[O:15])[NH:20][N:21]=2)=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20507196beta-(p-Chloroacetylaminobenzoyl)-propionic acid

Product 1

HCID 6771076-(p-Chloroacetylaminophenyl)-4,5-dihydropyridaz-3-oneYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.0 g (14.8 millimoles) of β-(p-chloroacetylaminobenzoyl)-propionic acid are refluxed with 0.74 g (14.8 millimoles) of hydrazine hydrate and 70 ml of ethanol for 3 hours. After filtering off the product at 10° C. and drying it under reduced pressure at 50° C., 3.3 g (84% of theory) of 6-(p-chloroacetylaminophenyl)-4,5-dihydropyridaz-3-one are obtained as pale yellow crystals (identical with the compound from Example 1, according to its melting point and infrared and NMR spectra).

Workup

  1. filtrationAfter filtering off the product at 10° C.
  2. customdrying it under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-e56cdb0533a047cd903e84995ef620f6
Source dataset
uspto-grants-1983_03
Patent number
US04376771

Reaction notes

Loading…