Ethylene Glycol → 2-tert-Butyl-5-hydroxy-4-methylpyridazin-3(2H)-one

HRID 2352018Notes

Reaction equation

HRID 2352018 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([O:13]CC)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].C(O)CO.Cl>O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([OH:13])[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13825163HCID 13825163, compound

Product 1

HCID 547131062-tert-Butyl-5-hydroxy-4-methylpyridazin-3(2H)-oneYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The resulting 2-tert.-butyl-5-ethoxy-4-methyl-3(2H)-pyridazinone (1.7 g) and potassium hydroxide (6.0 g) were added to 30 ml of ethyleneglycol, and the mixture was stirred under reflux for 3 hours. The reaction mixture was poured into 200 ml of water and added with 30 ml of 6N-hydrochloric acid. The crystals thus precipitated was collected by filtration. After drying, the crystals were washed with hot hexane to give 1.3 g of 2-tert.-butyl-5-hydroxy-4-methyl-3(2H)-pyridazinone. The melting point and the result of NMR analysis of this product were identical with those of the product obtained by the Method A.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe crystals thus precipitated
  3. filtrationwas collected by filtration
  4. customAfter drying
  5. washthe crystals were washed with hot hexane

Sources & evidence

ORD record
ord-d168dff946a84fcf835a660f85fe4b24
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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