2-Methyl-3-nitroaniline → 4-Nitroindazole

HRID 2092171Notes

Reaction equation

HRID 2092171 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) in acetic acid (˜200 mL) was treated with NaNO2 (20 g) in water (50 mL) at 4° C. (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. stirringstir overnight
  2. customThe solvent was removed under reduced pressure
  3. additionThe residue was treated with water (700 mL)
  4. filtrationthe mixture was filtered
  5. customThe solid was dried at 45° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-cdfe668e6da344f48dd61382cf386c99
Source dataset
uspto-grants-2013_05
Patent number
US08440691B2

Reaction notes

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