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

HRID 1392863Notes

Reaction equation

HRID 1392863 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-d04b7fb5b8454af49db4962eac323f53
Source dataset
uspto-grants-2008_03
Patent number
US07344702B2

Reaction notes

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