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

HRID 2046015Notes

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

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 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. Yield: 0.85 g (60% of theory). Mass spectrum (ESI+): m/z=185/187 (CI) [M+H]+

Workup

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

Sources & evidence

ORD record: ord-9d064c22054f4188b60995e6549c471a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592410B2

Reaction notes

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