Hydrochloric Acid → 2-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-one

HRID 1516090Notes

Reaction equation

HRID 1516090 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9](Cl)=[C:8]([Cl:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][Mg]Br.Cl>CCOCC>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:14])=[C:8]([Cl:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 138222642-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

2-tert-butyl-4,5-dichloro-3(2H)-pyridazinone (5 g, 22.72 mmol) dissolved in 12 ml of ether was added dropwise to 15 ml of a ether solution of methylmagnesium bromide (3M in ether) at 5° C. was added. After completion of addition the solution was stirred at 5° C. for 2 hours. 10 ml of 6N HCl solution is then added slowly to it and the solution is stirred for 10 minutes. The mixture is then extracted with diethyl ether. The ether layer is then washed with water and dried. The crude product obtained after concentrating the ether is subjected to flash chromatography (silica gel; ethyl acetate/hexanes:9:1) to give the product.

Workup

  1. additionwas added
  2. additionAfter completion of addition the solution
  3. stirringthe solution is stirred for 10 minutes
  4. extractionThe mixture is then extracted with diethyl ether
  5. washThe ether layer is then washed with water
  6. customdried

Sources & evidence

ORD record
ord-ba99141f57544b0d8b9f670dc99b9620
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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