Cyclohexylhydrazine hydrochloride → Ethyl 1-cyclohexyl-5-(4-benzyloxyphenyl)-1H-pyrazole-3-carboxylate

HRID 2216508Notes

Reaction equation

HRID 2216508 reaction equation
O/[C:2](=[CH:8]\[C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.[CH:26]1([NH:32][NH2:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>CCO.CCOC(C)=O>[CH:26]1([N:32]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][CH:11]=3)=[CH:8][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:33]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 2

HCID 207836Cyclohexylhydrazine hydrochlorideHCID 178473090HCID 178473090, compound

Product 1

HCID 11327171Ethyl 1-cyclohexyl-5-(4-benzyloxyphenyl)-1H-pyrazole-3-carboxylateYield 98.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The butenoate 1.2 (5.00 g, 15.3 mmol) and cyclohexylhydrazine hydrochloride (2.77 g, 18.4 mmol) were heated at refluxed in EtOH (60 ml) for 2 h. Concentration in vacuo resulted in formation of a solid which was suspended in EtOAc and filtered through a 1″ pad of SiO2, elution with ethyl acetate. The filtrate was concentrated to afford 6.10 g (98%) of the desired pyrazole ester 1.3. MS (ESI) 405.4 (M+H+).

Workup

  1. concentrationConcentration in vacuo
  2. customresulted in formation of a solid which
  3. filtrationfiltered through a 1″
  4. washpad of SiO2, elution with ethyl acetate
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-79572d6347054e7aa43d076ebd28c047
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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