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

HRID 579242Notes

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:23])[N:14]([CH3:22])[N:15]=[C:16]([CH3:21])[C:17]=1S(C)=O)[CH3:2].CS(C)=[O:26].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>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:23])[N:14]([CH3:22])[N:15]=[C:16]([CH3:21])[C:17]=1[OH:26])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a 50 ml volume three-necked flask, 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfinyl-2,3-dihydro-3-pyridazinone ((2-19)-(1)-39) (0.60 g), DMSO (2.73 ml), and 10% of aqueous tetra-n-butylammonium hydroxide solution (9.4 g) were added under a nitrogen atmosphere, and stirred at 90° C. for 2 hours. The reaction mixture was added to water and hydrochloric acid was added to adjust pH to less than 2. The resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform) to give 0.33 g of 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-39).

Workup

additionwas added
extractionThe resulting mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5648960d1e7a42b0a95d09bfc6b757f4
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040709B2

Reaction notes

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