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

HRID 51103

Reaction equation

HRID 51103 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-af99289b0e194dfda3f7b24fe115c883
Source dataset
uspto-grants-2004_03
Patent number
US06713485B2

Linked notes

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