Reaction #2286305

Reaction equation

2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester

acetic acid 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester

sodium hydroxide

→

6-[2,6-dichloro-4-(2-hydroxy-ethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-one

Yield 101.0%

6-[2,6-Dichloro-4-(2-hydroxyethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-one

Yield 101.0%

Solvents

methanol

Conditions

Workup

1. 1
   Concentrationwas then concentrated under vacuum
2. 2
   workup.ADDITIONThe resulting residue was diluted with methylene chloride (35 mL)
3. 3
   Washwas washed with a saturated aqueous sodium chloride solution (20 mL)
4. 4
   OtherThe aqueous layer was separated
5. 5
   Extractionwas re-extracted with methylene chloride (25 mL)
6. 6
   Dryingdried with sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   OtherThe resulting solid was dried under high vacuum

Procedure

A solution of 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester (35) (390 mg, 0.97 mmol) in methanol (4 mL) was treated with a 1N aqueous sodium hydroxide solution (1.0 mL, 1.0 mmol) at room temperature. The reaction mixture was stirred for 24 h and was then concentrated under vacuum. The resulting residue was diluted with methylene chloride (35 mL) and was washed with a saturated aqueous sodium chloride solution (20 mL). The aqueous layer was separated and was re-extracted with methylene chloride (25 mL). The organic layers were combined and dried with sodium sulfate, filtered, and concentrated. The resulting solid was dried under high vacuum to afford 6-[2,6-dichloro-4-(2-hydroxy-ethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-one (36) (350 mg, 97%) as a white solid that was used without further purification. Molecular Weight=357.2395; Exact Mass=356.0694

Source