4-Iodo-o-toluidine → 5-Iodo-1H-indazole

HRID 2390430Notes

Reaction equation

HRID 2390430 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[N:10]([O-])=O.[Na+]>C(O)(=O)C.O>[I:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:7][CH:8]=1)[NH:6][N:10]=[CH:9]2

Participants

5

Reactant 2

HCID 832214-Iodo-o-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 218947395-Iodo-1H-indazoleYield 99.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4-iodo-2-methylaniline (10.0 g, 42.9 mmol) in glacial acetic acid (400 mL) was treated with a solution of NaNO2 (2.96 g, 42.9 mmol) in water (10 mL). After stirring for 6 hours, the mixture was concentrated to dryness and dissolved in ethyl acetate (EtOAc). Filtration through a pad of silica gel (EtOAc) provided the title compound (10.4 g, 99%) as a deep purple solid: ESI MS m/z 245 [M+H]+.

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. dissolutiondissolved in ethyl acetate (EtOAc)
  3. filtrationFiltration through a pad of silica gel (EtOAc)

Sources & evidence

ORD record
ord-5d1d90d88e5e4b6ba772c7dff3fe43d4
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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