6-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one → HCID 13193380, compound

HRID 463655Notes

Reaction equation

HRID 463655 reaction equation
[C:1]([CH2:3][C:4](Cl)=[O:5])#[N:2].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:15][CH2:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:10][CH:9]=1>O1CCCC1>[C:1]([CH2:3][C:4]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:15][CH2:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:10][CH:9]=1)=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-oneHCID 110515942-Cyanoacetyl chloride

Product 1

HCID 13193380HCID 13193380, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.9 g (57.0 millimoles) of cyanoacetyl chloride were added dropwise to 6.0 g (31.7 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone in 150 ml of absolute tetrahydrofuran at room temperature, while stirring. After the addition was complete, stirring was continued for a further 10 minutes at 50° C. The product was filtered off under suction at 10° C., washed first with tetrahydrofuran and then with water and recrystallized from dimethylformamide/water. 4.4 g (54%) of 6-[p-(cyanoacetylamino)-phenyl]-4.5,-dihydro-3(2H)-pyridazinone were obtained as pale beige crystals. Mp.: 270° C. (decomposition).

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. filtrationThe product was filtered off under suction at 10° C.
  4. washwashed first with tetrahydrofuran
  5. customwith water and recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-94ed8b954ebf4babac871bcc0ed0f9f7
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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