Sodium Hydroxide → 6-[2,6-Dichloro-4-(2-hydroxy-ethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-one

HRID 2199123Notes

Reaction equation

HRID 2199123 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21][CH2:22][O:23]C(=O)C)[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[N:11]([CH3:19])[N:10]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:21][CH2:22][OH:23])[CH:5]=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:18])[N:11]([CH3:19])[N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59834451Acetic acid 2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester

Product 1

HCID 598344796-[2,6-Dichloro-4-(2-hydroxy-ethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-oneYield 101%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

Workup

  1. concentrationwas then concentrated under vacuum
  2. additionThe resulting residue was diluted with methylene chloride (35 mL)
  3. washwas washed with a saturated aqueous sodium chloride solution (20 mL)
  4. customThe aqueous layer was separated
  5. extractionwas re-extracted with methylene chloride (25 mL)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting solid was dried under high vacuum

Sources & evidence

ORD record
ord-ca9268419aaa4f149b1f3e12b2258951
Source dataset
uspto-grants-2016_06
Patent number
USRE046024E1

Reaction notes

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