Sulfuric Acid → 4-(2,6-Diethyl-4-methylphenyl)-5-methoxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone

HRID 335463Notes

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](=O)[C:13]([N:15]([CH3:24])[N:16]=[C:17]([CH3:23])[CH2:18]S(C)(=O)=O)=O)[CH3:2].[OH2:26].[OH-:27].[Li+].[OH-].[Na+].S(=O)(=O)(O)O.[C:36]1(C)C=CC=CC=1>O.CO>[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:27])[N:15]([CH3:24])[N:16]=[C:17]([CH3:23])[C:18]=1[O:26][CH3:36])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 25 mL volume three-necked flask, 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(1)-39) (1.00 g) and methanol (3.8 ml) were added under a nitrogen atmosphere, and cooled to 0° C. To the mixture was added toluene (1.15 g) and lithium hydroxide monohydrate (56 mg). After the mixture was stirred at 0° C. for 4 hours and at 5 for 16 hours, 48 w/w % of aqueous sodium hydroxide solution (445 mg) was added at 5° C., and stirred at room temperature for 1.5 hours and at 60° C. for 3 hours. To the mixture, water and toluene were added, then 20 w/w % of sulfuric acid was added to adjust pH to less than 1. After the organic layer was removed, the aqueous layer was extracted with toluene 2 times. The organic layers were combined, washed with saturated brine, and concentrated under reduced pressure to give 746 mg of 4-(2,6-diethyl-4-methylphenyl)-5-methoxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone (31-b).

Workup

stirringstirred at room temperature for 1.5 hours and at 60° C. for 3 hours
customAfter the organic layer was removed
extractionthe aqueous layer was extracted with toluene 2 times
washwashed with saturated brine
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e6992135335e4cb1b85e3225dbbe256b
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

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