2-Methyl-3-nitroaniline → 4-Nitroindazole

HRID 1911264Notes

Reaction equation

HRID 1911264 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+]>C(O)(=O)C.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-Nitroindazole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2-Methyl-3-nitroaniline (20.0 g, 131 mmol) in acetic acid (200 mL) was treated with NaNO2 (20.0 g, 289 mmol) in water (50 mL) at 4° C. (mechanical stirring). The reaction mixture was allowed to warm to ambient temperature and was stirred for 16 h. Solvent was removed under reduced pressure, and the residue was treated with water (700 mL), and filtered. The filtered solid was dried at 45° C. in a vacuum oven for 10 h to provide the title compound which was used without further purification.

Workup

  1. stirringwas stirred for 16 h
  2. customSolvent was removed under reduced pressure
  3. additionthe residue was treated with water (700 mL)
  4. filtrationfiltered
  5. customThe filtered solid was dried at 45° C. in a vacuum oven for 10 h

Sources & evidence

ORD record
ord-ec32282babd6473a953ecdc5720c743a
Source dataset
uspto-grants-2013_12
Patent number
US08604053B2

Reaction notes

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