2-Methyl-3-nitroaniline → 4-Nitroindazole

HRID 645716Notes

Reaction equation

HRID 645716 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[N:12]([O-])=O.[Na+]>CC(O)=O.O>[N+:9]([C:8]1[CH:7]=[CH:6][CH:5]=[C:3]2[C:2]=1[CH:1]=[N:12][NH:4]2)([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 117832-Methyl-3-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 180574-NitroindazoleYield 82.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a first step, to a solution of 2-methyl-3-nitroaniline (5 g, 32.86 mmol) in AcOH (100 ml) at 0° C. was added a solution of NaNO2 (5 g, 73.3 mmol) in water (45 ml), after stirring at room temperature for 15 h, the solution was concentrated, and the residue was suspended in water, the solid was collected by filtration to give 4-nitroindazole (4.4 g).

Workup

  1. concentrationthe solution was concentrated
  2. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-8f82dbc0641548f98a3cb064c747d7d9
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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