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

HRID 335458Notes

Reaction equation

HRID 335458 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 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 times
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efb939b6c1bc4e47aa06ae120559235d
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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