6-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one → HCID 53950990, compound

HRID 647813Notes

Reaction equation

HRID 647813 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.[Br:15][C@@H:16]1[CH2:18][C@H:17]1[C:19](Cl)=[O:20]>O1CCCC1>[Br:15][C@@H:16]1[CH2:18][C@H: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 54480682HCID 54480682, compound

Product 1

HCID 53950990HCID 53950990, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.0 g (21.1 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone of trans-2-bromocyclopropanecarboxylic acid chloride, 4.3 g (23.4 millimoles) and 100 ml of absolute tetrahydrofuran are kept for 20 hours at room temperature and then refluxed for 6 hours. The product is filtered off at 10° C., washed with water and recrystallized from dimethylformamide/water. 4.1 g (58% of theory) of trans-6-[p-(2-bromocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone are obtained as colorless crystals, of melting point 260°-261° C. (with decomposition).

Workup

  1. temperaturerefluxed for 6 hours
  2. filtrationThe product is filtered off at 10° C.
  3. washwashed with water
  4. customrecrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-5f2da973047b41b79ef8644c25fc590c
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Reaction notes

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