Water → 3,6-Dichloro-4-pyrrolidin-1-ylpyridazine

HRID 47226Notes

Reaction equation

HRID 47226 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[Cl:9].C(=O)([O-])[O-].[K+].[K+].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.O>CN(C=O)C>[Cl:9][C:3]1[N:4]=[N:5][C:6]([Cl:8])=[CH:7][C:2]=1[N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 220306484-Bromo-3,6-dichloropyridazine

Product 1

HCID 124492983,6-Dichloro-4-pyrrolidin-1-ylpyridazineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 4-bromo-3,6-dichloropyridazine (115 g, 0.51 mol) and potassium carbonate (209 g, 1.5 mol) in DMF (1) was added pyrrolidine (46 ml, 0.56 mol) at 0° C. with stirring. The mixture was allowed to warm to room temperature and then stirred under nitrogen overnight. Water (1.5) was added and the resultant slurry was filtered. The residue was washed thoroughly with water and diethyl ether, yielding the title compound (110 g, 100%) as a fine white powder. 1H NMR (250 MHz, CDCl3) δ2.03 (4H, m), 3.64 (4H, m), 6.46 (1H, s). MS (ES+) m/e 218 [MH]+, 220 [MR]+.

Workup

  1. stirringstirred under nitrogen overnight
  2. filtrationthe resultant slurry was filtered
  3. washThe residue was washed thoroughly with water and diethyl ether

Sources & evidence

ORD record
ord-19e3e5e315cc4e969cae033369497abb
Source dataset
uspto-grants-2004_03
Patent number
US06699859B1

Reaction notes

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