Bromine → HCID 12726872, compound

HRID 1764639Notes

Reaction equation

HRID 1764639 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[NH:5][N:4]=[C:3]1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13].BrBr>C(O)(=O)C>[CH3:1][C:2]1[C:3]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[N:4][NH:5][C:6](=[O:8])[CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 12726871HCID 12726871, compound

Product 1

HCID 12726872HCID 12726872, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A 15 g. portion of m-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)benzonitrile [Journal of Medicinal Chemistry 17, 281 (1974)] is suspended in 75 ml. of glacial acetic acid with stirring at steam bath temperature. Then 3.75 ml. of bromine in 25 ml. of acetic acid is added dropwise over a 15 minute period. The reaction mixture is heated on a steam bath for an additional 30 minutes then is poured onto crushed ice. The resulting solid is collected by filtration, copiously washed with water and dried to afford m-(1,6-dihydro-4-methyl-6-oxo-3-pyridazinyl)benzonitrile as a cream colored solid.

Workup

  1. temperatureThe reaction mixture is heated on a steam bath for an additional 30 minutes
  2. additionthen is poured
  3. customonto crushed ice
  4. filtrationThe resulting solid is collected by filtration
  5. washcopiously washed with water
  6. customdried

Sources & evidence

ORD record
ord-a569e2d298f84f479811b3df41ec4c21
Source dataset
uspto-grants-1978_09
Patent number
US04117130

Reaction notes

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