Ici 109,081 → HCID 20483374, compound

HRID 647804Notes

Reaction equation

HRID 647804 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.[CH3:16][C:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1>O1CCCC1>[CH3:15][CH:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:20]([C:17]3([CH3:16])[CH2:19][CH2:18]3)=[O:21])=[CH:3][CH:4]=2)=[N:13][NH:12][C:11](=[O:14])[CH2:10]1

Participants

4

Reactant 2

HCID 161928Ici 109,081HCID 127899391-Methylcyclopropane-1-carbonyl chloride

Product 1

HCID 20483374HCID 20483374, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

6.0 g (29.5 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are dissolved in 150 ml of absolute tetrahydrofuran by stirring and heating to 60° C. 4.2 g (35.4 millimoles) of 1-methylcyclopropanecarboxylic acid chloride are added dropwise to the above solution at 60° C., and the reaction mixture is then stirred for 7 hours at the reflux temperature. The product is filtered off at 10° C., washed with water and recrystallized twice from dimethylformamide/water. 5.5 g (65% of theory) of 4,5-dihydro-5-methyl-6-[p-(1-methylcyclopropylcarbonylamino)-phenyl]-3(2H)-pyridazinone are obtained as almost colorless crystals, of melting point 235°-237° C.

Workup

  1. stirringthe reaction mixture is then stirred for 7 hours at the reflux temperature
  2. filtrationThe product is filtered off at 10° C.
  3. washwashed with water
  4. customrecrystallized twice from dimethylformamide/water

Sources & evidence

ORD record
ord-4d27856f29204d2f9c1ed270ef4b1617
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Reaction notes

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