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

HRID 335444Notes

Reaction equation

HRID 335444 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:24])[N:14]([CH3:23])[N:15]=[C:16]([CH3:22])[C:17]=1S(C)(=O)=O)[CH3:2].C1(C)C=CC=CC=1.C[O:33]CCOCCOC.[OH-].[Na+]>O>[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:24])[N:14]([CH3:23])[N:15]=[C:16]([CH3:22])[C:17]=1[OH:33])[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8150DiglymeHCID 14798Sodium HydroxideHCID 569427174-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone

Product 1

HCID 546837784-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinoneYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a 100 mL volume four-necked flask, 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydropyridazin-3-one ((2-34)-(1)-39) (6.57 g), toluene (16.7 g), diethylene glycol dimethylether (3.6 g), and sodium hydroxide (2.86 g) were added under a nitrogen atmosphere, and stirred at 120° C. for 15 hours. Then, water (24.2 g) was added at room temperature. The organic layer was removed, and then the aqueous layer was mixed with 3.5 w/w % of hydrochloric acid (25 g) at the same temperature, and filtered. The residue was washed with water (12 g) and dried to give 4.7 g of 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-39).

Workup

  1. customThe organic layer was removed
  2. additionthe aqueous layer was mixed with 3.5 w/w % of hydrochloric acid (25 g) at the same temperature
  3. filtrationfiltered
  4. washThe residue was washed with water (12 g)
  5. customdried

Sources & evidence

ORD record
ord-ea36538632a842bfa122517399e25018
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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