HCID 23336376, compound → HCID 23336378, compound

HRID 903547Notes

Reaction equation

HRID 903547 reaction equation
[OH:1][CH:2]([CH:18]([CH3:20])[CH3:19])[CH2:3][N:4]1[C:9](=[O:10])[CH2:8][CH2:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:5]1>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:19][CH:18]([CH3:20])[C:2](=[O:1])[CH2:3][N:4]1[C:9](=[O:10])[CH2:8][CH2:7][C:6]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[N:5]1

Participants

5

Reactant 1

HCID 23336376HCID 23336376, compound

Product 1

HCID 23336378HCID 23336378, compound

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 7.0 grams (0.024 mol) of 2-(2-hydroxy-3-methylbutyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone in 2.4 milliliters of acetic acid is cooled with stirring in an icebath, and then over a period of about 5 minutes a solution of 2.2 grams (0.022 mol) of chromium trioxide in 45 milliliters of water is added. The reaction mixture is allowed to stir at room temperature for about 3 hours and then poured onto about 100 milliliters icewater. The mixture is extracted twice with 50 milliliters of methylene chloride and the organic layer is then washed with 30 milliliters of 2 N sodium hydroxide, water, and dried with anhydrous sodium sulfate. After filtration and evaporation to an oil, the product is crystallized from ether to 1.3 grams of 2-(3-methyl-2-oxobutyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone, (m.p. 110°-111° C.)

Workup

  1. stirringto stir at room temperature for about 3 hours
  2. additionpoured onto about 100 milliliters icewater
  3. extractionThe mixture is extracted twice with 50 milliliters of methylene chloride
  4. washthe organic layer is then washed with 30 milliliters of 2 N sodium hydroxide, water
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter filtration and evaporation to an oil
  7. customthe product is crystallized from ether to 1.3 grams of 2-(3-methyl-2-oxobutyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone, (m.p. 110°-111° C.)

Sources & evidence

ORD record
ord-acf2ccdbd87f4d14aa625f595b6bb79c
Source dataset
uspto-grants-1980_10
Patent number
US04228166

Reaction notes

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