Cyclopropanecarbonyl chloride → 6-(p-cyclopropylcarbonylaminophenyl)-4,5-dihydro-3(2H)-pyridazinone

HRID 647800Notes

Reaction equation

HRID 647800 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH:15]1([C:18](Cl)=[O:19])[CH2:17][CH2:16]1>C1(C)C=CC=CC=1>[CH:15]1([C:18]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][CH:3]=2)=[O:19])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 128073306-(p-cyclopropylcarbonylaminophenyl)-4,5-dihydro-3(2H)-pyridazinoneYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.0 g (31.7 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone and 4.0 g (38.3 millimoles) of cyclopropanecarboxylic acid chloride in 100 ml of absolute toluene are kept for 6 hours at 80° C. The product is filtered off at 10° C., washed first with toluene and then with water, and recrystallized from dimethylformamide/water. 5.0 g (61% of theory) of 6-(p-cyclopropylcarbonylaminophenyl)-4,5-dihydro-3(2H)-pyridazinone are obtained as colorless crystals, of melting point 272°-273° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed first with toluene
  3. customwith water, and recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-b496bda8b7284254b3fc6c7a7a5c369b
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Reaction notes

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