Hydrochloric Acid → 4-[5-(4-Chlorophenyl)-2-ethylphenyl]-5-methoxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone

HRID 579271Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:28][CH3:29])=[C:12]([C:14](=O)[C:15]([N:17]([CH3:26])[N:18]=[C:19]([CH3:25])[CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])=[O:16])[CH:13]=2)=[CH:4][CH:3]=1.[C:30]1(C)C=CC=CC=1.[OH2:37].[OH-:38].[Li+].[ClH:40]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:28][CH3:29])=[C:12]([C:14]3[C:15](=[O:16])[N:17]([CH3:26])[N:18]=[C:19]([CH3:25])[C:20]=3[S:21]([CH3:24])(=[O:23])=[O:22])[CH:13]=2)=[CH:4][CH:3]=1.[Cl:40][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:28][CH3:29])=[C:12]([C:14]3[C:15](=[O:38])[N:17]([CH3:26])[N:18]=[C:19]([CH3:25])[C:20]=3[O:37][CH3:30])[CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 25 ml volume three-necked flask, 1-[2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(1)-67) (853 mg), toluene (1.76 ml), and methanol (1.85 ml) were added under a nitrogen atmosphere, then added lithium hydroxide monohydrate (83 mg) at 0° C. After the mixture was stirred at 0° C. for 3 hours, 10 w/w % of hydrochloric acid was added to adjust pH to less than 1, and extracted with toluene 3 times. The organic layers were combined, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=3:1) to give 349 mg of 4-[5-(4-chlorophenyl)-2-ethylphenyl]-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(1)-67) and 66 mg of 4-[5-(4-chlorophenyl)-2-ethylphenyl]-5-methoxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone (31-a).

Workup

customat 0° C
extractionextracted with toluene 3 times
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d3e5e625c450439393044e1e9f281018
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040709B2

Reaction notes

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