(4-Chlorophenyl)hydrazine → [2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl ester

HRID 1678617Notes

Reaction equation

HRID 1678617 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:30])[CH:14]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:15](=O)[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=O)[CH3:11]>C(O)C>[CH2:10]([O:12][C:13](=[O:30])[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[C:16]=1[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH3:11]

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 671312392-Cyclohexyl-3-oxo-3-(2-oxo-cyclohexyl)-propionic acid ethyl ester

Product 1

HCID 67131110[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid ethyl esterYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Chloro-phenyl)-hydrazine (100 mg, 700 μmol; CAS Reg. No. 1073-69-4) was added to a solution of 2-cyclohexyl-3-oxo-3-(2-oxo-cyclohexyl)-propionic acid ethyl ester (206 mg, 700 μmol) in ethanol (4.7 ml). The reaction mixture was heated under reflux conditions for 6 h. The solvent was removed under reduced pressure. The residue was taken up in ice water/brine 1/1 and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give a brown oil which was purified by preparative thick layer chromatography (silica gel, iPrOAc/heptane) to give the title compound (130 mg, 324 μmol; 46%) as orange solid. MS: m/e=401.2 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions for 6 h
  2. customThe solvent was removed under reduced pressure
  3. extractionextracted two times with iPrOAc
  4. washThe combined extracts were washed with ice water/brine 1/1
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed under reduced pressure
  8. customto give a brown oil which
  9. customwas purified by preparative thick layer chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-1c10a462a35d4f638dc88c076aa946b2
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

Loading…