2-Methyl-3-nitroaniline → 4-Nitroindazole

HRID 2098593Notes

Reaction equation

HRID 2098593 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

To a solution of 2-methyl-3-nitroaniline (2.27 g, 14.91 mmol) in acetic acid (60 mL) was added a solution of sodium nitrite (1.13 g, 1.1 eq.) in water (5 mL). After 2 h, the deep red solution was poured onto ice/water and the resulting precipitate collected by filtration to yield 4-nitro-1H-indazole C (1.98 g, 81%).

Workup

  1. additionthe deep red solution was poured onto ice/water
  2. filtrationthe resulting precipitate collected by filtration

Sources & evidence

ORD record
ord-09efbc083d8140df9fafd4515e5e5a0f
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

Loading…