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

HRID 647806Notes

Reaction equation

HRID 647806 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([CH3:23])[CH2:19][CH:18]1[C:20](Cl)=[O:21]>O1CCCC1>[CH3:16][C:17]1([CH3:23])[CH2:19][CH:18]1[C:20]([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:21]

Participants

4

Reactant 2

HCID 161928Ici 109,081HCID 110079512,2-Dimethylcyclopropanecarbonyl chloride

Product 1

HCID 128073344,5-dihydro-6-[p-(2,2-dimethylcyclopropylcarbonylamino)-phenyl]-5-methyl-3(2H)-pyridazinoneYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using a method similar to that of Example 4, 6.0 g (29.5 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are reacted with 4.7 g (35.4 millimoles) of 2,2-dimethylcyclopropanecarboxylic acid chloride in 150 ml of absolute tetrahydrofuran. The mixture is concentrated to about 70 ml, water is added and the product is filtered off, washed with water and recrystallized twice from dimethylformamide/water, giving 5.8 g (66% of theory) of 4,5-dihydro-6-[p-(2,2-dimethylcyclopropylcarbonylamino)-phenyl]-5-methyl-3(2H)-pyridazinone as colorless crystals, of melting point 222°-223° C.

Workup

  1. concentrationThe mixture is concentrated to about 70 ml, water
  2. additionis added
  3. filtrationthe product is filtered off
  4. washwashed with water
  5. customrecrystallized twice from dimethylformamide/water

Sources & evidence

ORD record
ord-cc8d2efb075e4557a632886904c0efb0
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Reaction notes

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