Water → 5-Iodo-1H-indazole

HRID 1057118Notes

Reaction equation

HRID 1057118 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+].O>CC(O)=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 3

HCID 962WaterHCID 832214-Iodo-o-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 218947395-Iodo-1H-indazoleYield 78.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-iodo-2-methylaniline (1.09 g, 4.68 mmol) in CH3CO2H (40 mL), were added NaNO2 (0.39 g, 5.65 mmol) and water (1 mL) at 10° C. The resulting mixture was stirred at room temperature for 6 hours. Upon completion, the reaction mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0˜40% EtOAc in petroleum ether) affording the title compound (0.90 g). 1H NMR (DMSO-d6, 400 MHz): δ 13.23 (br, 1H), 8.18 (s, 1H), 8.02 (s, 1H), 7.57 (d, 1H), 7.41 (d, 1H).

Workup

  1. extractionUpon completion, the reaction mixture was extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (0˜40% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-fcb5e94b8a114ec9b62065133431f849
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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