tert-Butylhydrazine monohydrochloride → 6-(4-Chlorophenyl)-4,5-dihydro-2-t-butylpyridazinone

HRID 1560

Reaction equation

HRID 1560 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH:8]([CH3:12])C(O)=O)=O)=[CH:4][CH:3]=1.[C:15]([O-:18])(=O)C.[Na+].Cl.[C:21]([NH:25][NH2:26])([CH3:24])([CH3:23])[CH3:22]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[CH2:8][CH2:12][C:15](=[O:18])[N:25]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:26]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 517045Sodium AcetateHCID 189171154-Chlorobenzoylpropionic acid

Product 1

HCID 189171166-(4-Chlorophenyl)-4,5-dihydro-2-t-butylpyridazinoneYield 34.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 4-chlorobenzoylpropionic acid (4.24 g) in n-butanol (150 ml) was added anhydrous sodium acetate (1.54 g) and t-butylhydrazine hydrochloride (2.75 g) portionwise at room temperature. The resulting mixture was refluxed for 9 hours distilling off 65 ml of n-butanol during that time. The resulting mixture was cooled and poured into water (500 ml) and extracted with methylene chloride (3×150 ml). The combined organic layers were washed with 2% aqueous sodium hydroxide (3×100 ml), water (2×100 ml), 2% aqueous hydrochloric acid (3×100 ml), and water (1×100 ml), dried and evaporated under vacuum yielding 1.71 g of the expected product.

Workup

  1. temperatureThe resulting mixture was refluxed for 9 hours
  2. distillationdistilling off 65 ml of n-butanol during that time
  3. temperatureThe resulting mixture was cooled
  4. additionpoured into water (500 ml)
  5. extractionextracted with methylene chloride (3×150 ml)
  6. washThe combined organic layers were washed with 2% aqueous sodium hydroxide (3×100 ml), water (2×100 ml), 2% aqueous hydrochloric acid (3×100 ml), and water (1×100 ml)
  7. customdried
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-d1cec5adaec74900a26ae5c2339bc4da
Source dataset
uspto-grants-1998_03
Patent number
US05726176

Linked notes

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