Acetyl chloride → 5-Acetylamino-1-methyl-6-pyridazone

HRID 893182Notes

Reaction equation

HRID 893182 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[C:11](=[O:12])[N:10]([CH3:13])[N:9]=[CH:8][CH:7]=1>O1CCOCC1.N1C=CC=CC=1>[C:1]([NH:5][C:6]1[C:11](=[O:12])[N:10]([CH3:13])[N:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 131036364-Amino-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 146266165-Acetylamino-1-methyl-6-pyridazoneYield 58%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2.7 ml of acetyl chloride in 20 ml of dioxane was added dropwise to a solution of 4.0 g (0.032 mol) of 5-amino-1-methyl-6-pyridazone in 100 ml of pyridine. After stirring for 12 hours at 25° C., the solvent was distilled off under reduced pressure, and the residue was taken up with methylene chloride, washed with sodium bicarbonate solution and dried. After the solvent had been stripped off under reduced pressure and the residue stirred with a small amount of diisopropyl ether, there was obtained 3.1 g (58.0%) of 5-acetylamino-1-methyl-6-pyridazone (active ingredient 1.001) of melting point 152°-153° C.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. washwashed with sodium bicarbonate solution
  3. customdried
  4. stirringthe residue stirred with a small amount of diisopropyl ether

Sources & evidence

ORD record
ord-30ab794546f0402a8858c5bd6768c80b
Source dataset
uspto-grants-1992_06
Patent number
US05123952

Reaction notes

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