Potassium Hydroxide → HCID 58128652, compound

HRID 2088465Notes

Reaction equation

HRID 2088465 reaction equation
Cl[C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[CH3:22])[CH:10]=1.[OH-].[K+]>CN(C=O)C.O.[Pd]>[CH3:21][C:20]1[N:16]([C:11]2[CH:10]=[C:9]([C:3]3[C:4](=[O:8])[NH:5][N:6]=[CH:7][CH:2]=3)[CH:14]=[CH:13][C:12]=2[CH3:15])[C:17]([CH3:22])=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 58128653HCID 58128653, compound

Product 1

HCID 58128652HCID 58128652, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-4-[3-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-phenyl]-2H-pyridazin-3-one (0.90 g, 2.87 mmol) and KOH (0.40 g, 7.17 mmol) in DMF (1.2 ml) and water (11 ml) was added 10% Pd/C (0.05 g). The mixture was hydrogenated in a Parr vessel at 4.14 BAR for 18 hours. Aqueous 10% KOH (15 ml) was added and the mixture was filtered. The filtrate was take to pH 1 with conc. HCl and extracted with DCM. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/1:1) gave 0.429 g (54%) of 4-[3-(2,5-dimethyl-pyrrol-1-yl)-4-methyl-phenyl]-2H-pyridazin-3-one as a yellow solid.

Workup

  1. filtrationthe mixture was filtered
  2. extractionextracted with DCM
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification of the residue by flash chromatography (hex:EtOAc/1:1)

Sources & evidence

ORD record
ord-c6079caea11d454fa22a33434a311ddb
Source dataset
uspto-grants-2013_05
Patent number
US08435990B2

Reaction notes

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