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

HRID 2352012Notes

Reaction equation

HRID 2352012 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].Cl.[C:15]1(C)C=CC=CC=1>>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:15])=[C:8]([Cl:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-one

Product 1

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

Procedure

The resulting Grignard reagent was cooled to room temperature and was added dropwise over 20 minutes with 22.1 g (0.1 mol) of 2-tert.-butyl-4,5-dichloro-3(2H)-pyridazinone dissolved in 200 ml of dry toluene. After completion of adding, the reaction liquid was subjected to reaction for 1.5 hours at room temperature and then poured into a solution of 100 ml of conc. hydrochloric acid in 900 ml of ice-water to effect extraction. The resulting organic layer was then washed with 500 ml of 10% aqueous solution of sodium hydroxide and then with 500 ml of water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 17.2 g of a crude product. The crude product was subjected to distillation (boiling point: 60° to 62° C./0.22 mmHg) and then column chromatography (silica gel; hexane:acetone=15:1) for separation and purification to give 4.5 g of 2-tert.-butyl-5-chloro-4-methyl-3(2H)-pyridazinone.

Workup

  1. additionAfter completion of adding
  2. customthe reaction liquid
  3. customwas subjected to reaction for 1.5 hours at room temperature
  4. extractionextraction
  5. washThe resulting organic layer was then washed with 500 ml of 10% aqueous solution of sodium hydroxide
  6. dry with materialwith 500 ml of water, and dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto give 17.2 g of a crude product
  9. distillationThe crude product was subjected to distillation (boiling point: 60° to 62° C./0.22 mmHg)
  10. customcolumn chromatography (silica gel; hexane:acetone=15:1) for separation and purification

Sources & evidence

ORD record
ord-f845ec5f2a6a4432b608a1d6cfb23555
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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