Sodium Hydroxide → 5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole

HRID 69100

반응식

HRID 69100 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[N:11](C)C)=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1.Cl.[CH:19]1([NH:24]N)[CH2:23][CH2:22][CH2:21][CH2:20]1.O.C(OCC)(=O)C.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:24]([CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:11]=[CH:10][CH:9]=2)=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 212349Cyclopentylhydrazine hydrochlorideHCID 22728543Water ethylacetateHCID 86694307HCID 86694307, 화합물

생성물 1

HCID 866943065-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole수율 72.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Under a nitrogen atmosphere, to a solution of 1.15 g of (2E)-1-(4-bromo-2-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one in 9.2 mL of acetic acid was added 1.05 g of cyclopentylhydrazine hydrochloride, followed by stirring at room temperature for 60 hours. The reaction mixture was poured into a mixture of water/ethyl acetate, followed by adjusting to pH 10 with a 6 M aqueous sodium hydroxide solution. The aqueous layer was separated, and then the organic layer was washed with water 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 (n-hexane/ethyl acetate) to obtain 940 mg of 5-(4-bromo-2-nitrophenyl)-1-cyclopentyl-1H-pyrazole.

후처리

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-cf396f515aa44bb389aea08b1452c5fb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822448B2

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