6-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one → 6-[p-(1-chlorocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 647807Notes

Reaction equation

HRID 647807 reaction equation
[Cl:1][C:2]1([C:5](Cl)=[O:6])[CH2:4][CH2:3]1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:11][CH:10]=1>O1CCCC1>[Cl:1][C:2]1([C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=3)=[CH:11][CH:10]=2)=[O:6])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-oneHCID 10942508Cyclopropanecarbonyl chloride, 1-chloro-

Product 1

HCID 128073356-[p-(1-chlorocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.45 g (32.0 millimoles) of 1-chlorocyclopropanecarboxylic acid chloride in 20 ml of absolute tetrahydrofuran is added dropwise to a stirred suspension of 5.0 g (26.4 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone in 100 ml of absolute tetrahydrofuran. The mixture is then stirred for 20 hours at room temperature followed by 1 hour under reflux. The product is filtered off at 10° C., washed first with tetrahydrofuran and then with water, and recrystallized from dimethylformamide/water. 6.3 g (82% of theory) of 6-[p-(1-chlorocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone are isolated as colorless crystals, of melting point 231°-232° C.

Workup

  1. waitfollowed by 1 hour
  2. temperatureunder reflux
  3. filtrationThe product is filtered off at 10° C.
  4. washwashed first with tetrahydrofuran
  5. customwith water, and recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-e5b441ce7ce547e6b8c318d570741042
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Reaction notes

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