Triethylamine → 1-Benzyl-3-methyl-5-nitroindazole

HRID 2215694Notes

Reaction equation

HRID 2215694 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)=O.C(N(CC)CC)C.Cl.Cl.[CH2:23]([NH:30][NH2:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C>[CH2:23]([N:30]1[C:5]2[C:4](=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[CH:7][CH:6]=2)[C:2]([CH3:1])=[N:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 146540Benzylhydrazine dihydrochlorideHCID 27810671-(2-Fluoro-5-nitrophenyl)ethan-1-one

Product 1

HCID 219521621-Benzyl-3-methyl-5-nitroindazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Fluoro-5-nitroacetophenone (H. Sato et al, Bioorganic and Medicinal Chemistry Letters, 5(3), 233–236,1995) (0.24 g) was treated with triethylamine (0.73 ml) and benzyl hydrazine dihydrochloride (0.255 g) in ethanol (20 ml) at reflux under N2 for 8 days. The mixture was cooled and the solid 1-benzyl-3-methyl-5-nitroindazole (0.16 g) was collected by filtration; m/z (M+1)+ 268.

Workup

  1. temperatureat reflux under N2 for 8 days
  2. temperatureThe mixture was cooled
  3. filtrationthe solid 1-benzyl-3-methyl-5-nitroindazole (0.16 g) was collected by filtration

Sources & evidence

ORD record
ord-32e790fce3114e2eaff68c921f3faf16
Source dataset
uspto-grants-2006_09
Patent number
US07109333B2

Reaction notes

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