Ici 109,081 → 6-[p-(1-chlorocyclopropylcarbonylamino)phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone

HRID 647810Notes

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][C:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1>O1CCCC1>[Cl:16][C:17]1([C:20]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][CH:3]=2)=[O:21])[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 60 °C

Procedure

5.0 g (24.6 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are dissolved in 100 ml of absolute tetrahydrofuran by stirring and heating to 60° C. The solution is allowed to cool to room temperature, 4.15 g (29.9 millimoles) of 1-chlorocyclopropanecarboxylic acid chloride are added dropwise and the reaction solution is then stirred for 6 hours at room temperature. It is then concentrated to half its volume and 200 ml of water are added. The precipitate which forms is filtered off, washed with water and recrystallized from methanol, giving 5.5 g (73% of theory) of 6-[p-(1-chlorocyclopropylcarbonylamino)phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone as colorless crystals, of melting point 189°-190° C.

Workup

temperatureto cool to room temperature
stirringthe reaction solution is then stirred for 6 hours at room temperature
concentrationIt is then concentrated to half its volume and 200 ml of water
additionare added
filtrationThe precipitate which forms is filtered off
washwashed with water
customrecrystallized from methanol

Sources & evidence

ORD record: ord-4b36b1c527da462386eb043c8dd0f8db
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04410529

Reaction notes

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