2-Methyl-3-nitroaniline → 4-Nitroindazole

HRID 1517636Notes

Reaction equation

HRID 1517636 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 g, 129.0 mmol) in acetic acid (˜200 mL) was treated with NaNO2 (20 g, 290.0 mmol) in water (50 mL) at 4° C. with mechanical stirring. The reaction mixture was allowed to warm to room temperature and stir overnight. The solvent was removed under reduced pressure. The residue was treated with water (700 mL) and the mixture was filtered. The solid was dried at 45° C. in a vacuum oven overnight to provide the title compound. 1H NMR (DMSO-d6) δ 8.56 (s, 1H), 8.2-8.05 (dd, 2H), 7.6 (t, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was treated with water (700 mL)
  3. filtrationthe mixture was filtered
  4. customThe solid was dried at 45° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-efe3fce664a043298d5b08dc1ef07c3c
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

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