Methyl iodide → 1H-Indazole, 1-methyl-6-nitro-

HRID 2214193Notes

Reaction equation

HRID 2214193 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:15]I>C1COCC1>[CH3:15][N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH:8]=[N:9]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 242396-NitroindazoleHCID 24758Sodium hydride

Product 1

HCID 812901H-Indazole, 1-methyl-6-nitro-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-nitroindazole (8 g) in THF (200 ml) was added NaH (2.5 g) at 0° C. The reaction was stirred for 30 min and MeI (3.7 ml) was added and stirred at RT overnight. The reaction was quenched with water and extracted with EtOAc twice, then was further purified by column chromatography to give 1-methyl-6-nitro-1H-indazole which was hydrogenated with an H2 atmosphere in the presence of Pd/C (400 mg) to give 1-methyl-6-amino-1H-indazole.

Workup

  1. stirringstirred at RT overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc twice
  4. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-bc7e56b1fbea4db89dd93f873744066b
Source dataset
uspto-grants-2006_09
Patent number
US07105682B2

Reaction notes

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