Water → 6-Chloro-2-cyclopropylmethyl-2H-pyridazin-3-one

HRID 80951

Reaction equation

HRID 80951 reaction equation
[CH:1]1([CH2:4]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:8]=[CH:9][C:10](=[O:13])[NH:11][N:12]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10](=[O:13])[N:11]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 2528286-Chloropyridazin-3-ol

Product 1

HCID 581095136-Chloro-2-cyclopropylmethyl-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Cyclopropylmethyl bromide (0.82 mL) was added to a mixture of 6-chloro-2H-pyridazin-3-one (1.0 g) and K2CO3 (2.10 g) in N,N-dimethylformamide (10 mL). The resulting mixture was stirred at 60° C. overnight. Then, water was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine and dried (MgSO4). After removal of the solvent, the residue was purified by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 99:1:0.1) to afford the title compound as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customAfter removal of the solvent
  5. customthe residue was purified by chromatography on silica gel (CH2Cl2/MeOH/NH4OH 99:1:0.1)

Sources & evidence

ORD record
ord-5c941b44a5f24da98bbb55349a3ff332
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Linked notes

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