(4-(Benzyloxy)phenyl)hydrazine monohydrochloride → HCID 58256801, compound

HRID 1013044Notes

Reaction equation

HRID 1013044 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:13](=O)[CH3:14])[C:10](=O)[CH3:11])=[CH:5][CH:4]=1.Cl.[CH2:17]([O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C.O>[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]([N:31]2[C:13]([CH3:14])=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:10]([CH3:11])=[N:32]2)=[CH:29][CH:30]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochlorideHCID 125651523-(4-Methoxyphenyl)pentane-2,4-dione

Product 1

HCID 58256801HCID 58256801, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-(4-methoxyphenyl)pentane-2,4-dione (50 mg, 0.24 mmol, prepared according to Ghosh et al, Bioorg. Med. Chem. 2003, 11, 629) and (4-benzyloxyphenyl)hydrazine hydrochloride (61 mg, 0.24 mmol) in ethanol (3 mL) was heated at 80° C. overnight. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with 1 N HCl (2×) and saturated sodium bicarbonate (1×), dried (MgSO4), and concentrated to give 57 mg of the crude pyrazole. LC-MS (C25H24N2O2 calculated 384) m/z 385 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1 N HCl (2×) and saturated sodium bicarbonate (1×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe68828ad70240148707ec6f93c3da01
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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