Bromine → HCID 13424593, compound

HRID 372703Notes

Reaction equation

HRID 372703 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]([CH3:16])[CH2:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1)#[N:2].BrBr>C(O)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([CH3:16])=[CH:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 148530204-(4-Methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)benzonitrile

Product 1

HCID 13424593HCID 13424593, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A 5.0 g. portion of 6-(p-cyanophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone (prepared as described in Example 44 of U.S. Pat. No. 3,824,271) is slurried in 25 ml. of acetic acid. A solution of 1.4 ml. of bromine in 25 ml. of acetic acid is added and the reaction mixture is heated on a steam bath for 30 minutes. A 400 ml. portion of ice water is added and the resulting solid is collected by filtration. This product is heated in 200 ml. of a mixture of ethyl acetate and methanol at the boiling point and filtered free of insolubles. The filtrate is concentrated to about 75 ml., cooled in ice and the resulting white solid collected and dried, yielding 6-(p-cyanophenyl)-5-methyl-3(2H)-pyridazinone.

Workup

  1. temperaturethe reaction mixture is heated on a steam bath for 30 minutes
  2. filtrationthe resulting solid is collected by filtration
  3. temperatureThis product is heated in 200 ml
  4. additionof a mixture of ethyl acetate and methanol at the boiling point
  5. filtrationfiltered free of insolubles
  6. concentrationThe filtrate is concentrated to about 75 ml
  7. temperature, cooled in ice
  8. customthe resulting white solid collected
  9. customdried

Sources & evidence

ORD record
ord-e5b1dce23e1c42b08c098ae7b4dc968e
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Reaction notes

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