Acetic Acid → HCID 13424593, compound

HRID 1764632Notes

Reaction equation

HRID 1764632 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.C(O)(=O)C.BrBr.Br>O>[CH3:1][C:2]1[C:3]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[N:4][NH:5][C:6](=[O:8])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 24408Bromine2×HCID 148530204-(4-Methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)benzonitrile

Product 1

HCID 13424593HCID 13424593, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 200 g. portion of p-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)benzonitrile [Journal of Medicinal Chemistry 17, 281(1974)] is suspended in 500 ml. of glacial acetic acid with overhead stirring at steam bath temperature, then 56 ml. of liquid bromine is dissolved in an additional 500 ml. of acetic acid and this solution is added to the stirring mixture all at once. After approximately half an hour of heating, a vigorous exothermic reaction occurs with the expulsion of the excess bromine and hydrogen bromide. The reaction mixture is then diluted with 4 liters of distilled water and the resulting solid is filtered and the filter cake is copiously washed with water and is air dried. This material is recrystallized from a large amount of ethyl alcohol to afford the product p-(1,6-dihydro-4-methyl-6-oxo-3-pyridazinyl)benzonitrile as a white solid.

Workup

  1. temperatureAfter approximately half an hour of heating
  2. customa vigorous exothermic reaction
  3. filtrationthe resulting solid is filtered
  4. washthe filter cake is copiously washed with water
  5. customdried
  6. customThis material is recrystallized from a large amount of ethyl alcohol

Sources & evidence

ORD record
ord-a7184ea80a734469bd88b1e047ff3b31
Source dataset
uspto-grants-1978_09
Patent number
US04117130

Reaction notes

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