N-methyl-2-pyrrolidone → 4-[5-(4-Chlorophenyl)-2-ethylphenyl]-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone

HRID 579272Notes

Reaction equation

HRID 579272 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:27][CH3:28])=[C:12]([C:14]3[C:15](=[O:26])[N:16]([CH3:25])[N:17]=[C:18]([CH3:24])[C:19]=3S(C)(=O)=O)[CH:13]=2)=[CH:4][CH:3]=1.CN1CCCC1=[O:35].[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:27][CH3:28])=[C:12]([C:14]3[C:15](=[O:26])[N:16]([CH3:25])[N:17]=[C:18]([CH3:24])[C:19]=3[OH:35])[CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 666955554-[5-(4-Chlorophenyl)-2-ethylphenyl]-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone

Product 1

HCID 666956784-[5-(4-Chlorophenyl)-2-ethylphenyl]-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinoneYield 63.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a 25 ml volume three-necked flask, 4-[5-(4-chlorophenyl)-2-ethylphenyl]-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(1)-67) (290 mg), N-methyl-2-pyrrolidone (890 mg), and aqueous sodium hydroxide solution (410 mg) were added under a nitrogen atmosphere, and stirred at 70° C. for 3 hours. After the reaction mixture was cooled to room temperature, toluene was added and washed. The organic layer was removed. To the resulting aqueous layer, 10 wt % of hydrochloric acid was added to adjust pH to less than 1, and extracted with ethyl acetate 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=2:1) to give 157 mg of 4-[5-(4-chlorophenyl)-2-ethylphenyl]-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-67).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. washwashed
  3. customThe organic layer was removed
  4. additionTo the resulting aqueous layer, 10 wt % of hydrochloric acid was added
  5. extractionextracted with ethyl acetate 3 times
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b26d2319f6847cdbe0b0c92ff4756ff
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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