Reaction #1588

Reaction equation

4-chlorobenzoylpropionic acid

sodium acetate

t-butylhydrazine hydrochloride

→

expected product

Yield 34.4%

6-(4-chlorophenyl)-4,5-dihydro-2-t-butylpyridazinone

Yield 34.4%

Solvents

n-butanol

Conditions

Workup

1. 1
   TemperatureThe resulting mixture was refluxed for 9 hours
2. 2
   workup.DISTILLATIONdistilling off 65 ml of n-butanol during that time
3. 3
   TemperatureThe resulting mixture was cooled
4. 4
   workup.ADDITIONpoured into water (500 ml)
5. 5
   Extractionextracted with methylene chloride (3×150 ml)
6. 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. 7
   Otherdried
8. 8
   Otherevaporated under vacuum

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.

Source