2-Chloropropionyl chloride → 2-Chloro-4'-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)propionanilide

HRID 354678Notes

Reaction equation

HRID 354678 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[Cl:16][CH:17]([CH3:21])[C:18](Cl)=[O:19]>C1(C)C=CC=CC=1>[Cl:16][CH:17]([CH3:21])[C:18]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:19]

Participants

4

Reactant 2

HCID 1110192-Chloropropionyl chlorideHCID 161928Ici 109,081

Product 1

HCID 688892-Chloro-4'-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)propionanilideYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.0 g (29.6 millimoles) of 6-(p-aminophenyl)-5-methyl-4,5-dihydropyridaz-3-one and 4.1 g (32.3 millimoles) of 2-chloropropionyl chloride in 100 ml of absolute toluene are kept at 80° C. for 4 hours. The product is filtered off at 10° C., washed with water and dried under reduced pressure at 50° C. 7.9 g (91% of theory) of 6-[p-(2-chloropropionylamino)-phenyl]-5-methyl-4,5-dihydropyridaz-3-one are isolated as beige crystals which, after recrystallization from methanol, melt at 215°-217° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed with water
  3. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-508efb2aeeb94033a290e9b3fea57417
Source dataset
uspto-grants-1983_03
Patent number
US04376771

Reaction notes

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