Cyclopentylhydrazine hydrochloride → HCID 86694313, compound

HRID 69109

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[CH3:11])=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1.Cl.[CH:18]1([NH:23][NH2:24])[CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:23]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:24]=[C:10]([CH3:11])[CH:9]=2)=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Under a nitrogen atmosphere, to a solution of 1.0 g of 1-(4-bromo-2-nitrophenyl)butane-1,3-dione in 10 ml of acetic acid was added 501 mg of cyclopentylhydrazine hydrochloride, followed by stirring at 100° C. for 1 hour and 30 minutes. The reaction mixture was concentrated, and to the obtained residue was added ethyl acetate. The solution was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 770 mg of 5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-3-methyl-1H-pyrazole.

Workup

concentrationThe reaction mixture was concentrated
additionto the obtained residue was added ethyl acetate
washThe solution was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record: ord-a380d65bfdde4e3f8411965e030bc974
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822448B2

Linked notes

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