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

HRID 1751866Notes

Reaction equation

HRID 1751866 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-4ef46c46d5104465b2f416da74aa0e6e
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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