(4-Chlorophenyl)hydrazine → [2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid ethyl ester

HRID 889371Notes

Reaction equation

HRID 889371 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13](=[O:29])[CH:14]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:15](=O)[CH:16]1[CH2:20][CH2:19][CH2:18][C:17]1=O)[CH3:11]>C(O)C>[CH2:10]([O:12][C:13](=[O:29])[CH:14]([C:15]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[C:17]2[CH2:18][CH2:19][CH2:20][C:16]=12)[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[CH3:11]

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 673867762-Cyclohexyl-3-oxo-3-(2-oxo-cyclopentyl)-propionic acid ethyl ester

Product 1

HCID 67387258[2-(4-Chloro-phenyl)-2,4,5,6-tetrahydro-cyclopentapyrazol-3-yl]-cyclohexyl-acetic acid ethyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Chloro-phenyl)-hydrazine (5.63 g, 31 mmol; CAS Reg. No. 1073-69-4) was added to a solution of 2-cyclohexyl-3-oxo-3-(2-oxo-cyclopentyl)-propionic acid ethyl ester (8.8 g, 31 mmol) in ethanol (200 ml). The reaction mixture was heated under reflux conditions for 6 h. The solvent was removed under reduced pressure. The residue was suspended in dichloromethane and filtered off. The filtrate was brought to dryness under reduced pressure to give a brown oil which was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (6.26 g, 16 mmol; 51%) as orange oil. MS: m/e=388.4 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions for 6 h
  2. customThe solvent was removed under reduced pressure
  3. filtrationfiltered off
  4. customto give a brown oil which
  5. customwas purified by column chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-3c5ddd2cea6641158fd79ea59ed9f0fe
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

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