Potassium Hydroxide → HCID 59834464, compound

HRID 271179Notes

Reaction equation

HRID 271179 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][O:22]C(=O)C)[CH:5]=[C:6]([Br:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]([CH3:18])[CH3:17])[N:10]=1.[OH-].[K+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][OH:22])[CH:5]=[C:6]([Br:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]([CH3:18])[CH3:17])[N:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59834519HCID 59834519, compound

Product 1

HCID 59834464HCID 59834464, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2-[3,5-dibromo-4-(1-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester (40) (85 mg, 0.18 mmol) in methanol (0.5 mL) was treated with a 2N aqueous potassium hydroxide solution (90 μL, 0.18 mmol) at room temperature. The reaction mixture was heated to 55° C., stirred for 1 h and then was concentrated under reduced pressure. The resulting residue was diluted with methylene chloride (5 mL) and was washed with water (2×3 mL). The aqueous layers were re-extracted with methylene chloride (5 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-dibromo-4-(2-hydroxy-ethyl)-phenoxy]-2-isopropyl-pyridazin-3-one (41) (77 mg, 100%) as a white solid that was used without further purification; LRMS for C15H16Br2N2O3 (M+CH3CN+H) m/z=474. Molecular Weight=432.1144; Exact Mass=429.9528

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe resulting residue was diluted with methylene chloride (5 mL)
  3. washwas washed with water (2×3 mL)
  4. extractionThe aqueous layers were re-extracted with methylene chloride (5 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting solid was dried under high vacuum

Sources & evidence

ORD record
ord-26f75d3011dd4db8a2e5db7e1642e501
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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