6-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one → 4,5-dihydro-6-[p-(2,2-dimethylcyclopropylcarbonylamino)-phenyl]-3(2H)-pyridazinone

HRID 647805Notes

Reaction equation

HRID 647805 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.[CH3:15][C:16]1([CH3:22])[CH2:18][CH:17]1[C:19](Cl)=[O:20]>O1CCCC1>[CH3:15][C:16]1([CH3:22])[CH2:18][CH:17]1[C:19]([NH: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)=[O:20]

Participants

4

Reactant 2

HCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-oneHCID 110079512,2-Dimethylcyclopropanecarbonyl chloride

Product 1

HCID 128073334,5-dihydro-6-[p-(2,2-dimethylcyclopropylcarbonylamino)-phenyl]-3(2H)-pyridazinoneYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g (26.4 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone, 4.2 g (31.7 millimoles) of 2,2-dimethylcyclopropanecarboxylic acid chloride in 100 ml of absolute tetrahydrofuran are refluxed for 7 hours. The mixture is concentrated to about 50 ml and the product is filtered off at 10° C., washed with water and recrystallized from dimethylformamide/water. 5.2 g (68% of theory) of 4,5-dihydro-6-[p-(2,2-dimethylcyclopropylcarbonylamino)-phenyl]-3(2H)-pyridazinone quarter-hydrate are obtained as almost colorless crystals, of melting point 213°-214° C.

Workup

  1. concentrationThe mixture is concentrated to about 50 ml
  2. filtrationthe product is filtered off at 10° C.
  3. washwashed with water
  4. customrecrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-cd8db6b11eab40ceb06dde904201c28c
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Reaction notes

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