Sodium Hydroxide → 4-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

HRID 335449Notes

Reaction equation

HRID 335449 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:30])[N:14]([CH3:29])[N:15]=[C:16]([CH3:28])[C:17]=1S(C1C=CC(C)=CC=1)(=O)=O)[CH3:2].[OH-:31].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:30])[N:14]([CH3:29])[N:15]=[C:16]([CH3:28])[C:17]=1[OH:31])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 666955404-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-(4-methylphenylsulfonyl)-2,3-dihydro-3-pyridazinone

Product 1

HCID 546837784-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinoneYield 40.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

TO a 10 ml volume two-necked flask with Dean-Stark, 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-(4-methylphenylsulfonyl)-2,3-dihydro-3-pyridazinone ((2-36)-(1)-39) (699 mg), toluene (2.45 ml), tetrabutylammonium bromide (27 mg), and 48 w/w % of aqueous sodium hydroxide solution (550 mg) were added. Water was removed by azeotropic distillation under reflux for 33 hours. After the mixture was cooled to room temperature, water was added, and the organic layer was removed. To the aqueous layer, 20 w/w % of sulfuric acid was added to adjust pH to 4, and extracted with toluene 2 times. The organic layers were combined, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane:ethyl acetate=5:1) to give 189 mg of 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-39).

Workup

  1. customWater was removed by azeotropic distillation
  2. temperatureunder reflux for 33 hours
  3. additionwater was added
  4. customthe organic layer was removed
  5. additionTo the aqueous layer, 20 w/w % of sulfuric acid was added
  6. extractionextracted with toluene 2 times
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21afb3c1f520449bb9610bbc839a7a00
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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