Ethylenediamine → 4-(6-Oxo-1,6-dihydropyridazin-3-yl)benzonitrile

HRID 372690

Reaction equation

HRID 372690 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:15][N:16](C)C=O.C(N)CN>O>[C:15]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)#[N:16]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6228DimethylformamideHCID 6890736-(4-Bromophenyl)-2,3-dihydropyridazin-3-one

Product 1

HCID 194194914-(6-Oxo-1,6-dihydropyridazin-3-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 19.20 g. portion of 6-(p-bromophenyl)-3(2H)-pyridazinone is mixed with 9.10 g. of cuprous cyanide in 70 ml. of dimethylformamide and stirred at reflux temperature for 12 hours. The hot mixture is poured into a solution of 46 ml. of ethylenediamine in 230 ml. of water. The mixture is stirred at ice-bath temperature for 30 minutes and the solid is separated by filtration. A second crop forms in the filtrate which is collected and added to the first crop which is then washed with water yielding 6-(p-cyanophenyl)-3(2H)-pyridazinone.

Workup

  1. temperatureat reflux temperature for 12 hours
  2. additionThe hot mixture is poured into a solution of 46 ml
  3. customthe solid is separated by filtration
  4. customA second crop forms in the filtrate which is collected
  5. additionadded to the first crop which
  6. washis then washed with water

Sources & evidence

ORD record
ord-4296f7fe678e41928dd3210e7571eb17
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Linked notes

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