Dimethylformamide → 4-Chloro-1-mesityl-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one

HRID 598141Notes

Reaction equation

HRID 598141 reaction equation
[Cl:1][C:2]1[C:3]2[CH:11]=[CH:10][N:9]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[C:4]=2[C:5](=[O:8])[NH:6][N:7]=1.CI.[C:23](=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Cl:1][C:2]1[C:3]2[CH:11]=[CH:10][N:9]([C:12]3[C:13]([CH3:20])=[CH:14][C:15]([CH3:19])=[CH:16][C:17]=3[CH3:18])[C:4]=2[C:5](=[O:8])[N:6]([CH3:23])[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67267604HCID 67267604, compound

Product 1

HCID 672671274-Chloro-1-mesityl-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-oneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-1-mesityl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (0.43 g, 1.5 mmol), MeI (0.103 ml, 1.65 mmol), potassium carbonate (0.41 g, 3.0 mmol) and DMF (5 ml) was stirred at room temperature for 19 hours. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (50 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (3:1) to give 0.38 g (98%) of the title compound as crystals.

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-3ee7d72ded58460f97e972edf5074821
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

Loading…