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

HRID 1750885Notes

Reaction equation

HRID 1750885 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].I[CH3:16]>C1COCC1>[CH3:16][N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=2)[CH:10]=[N:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 242396-NitroindazoleHCID 24758Sodium hydride

Product 1

HCID 812901H-Indazole, 1-methyl-6-nitro-Yield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (1.47 g, 0.037 mol) was added to THF (25 mL) at 0° C. Separately, 6-nitro-1H-indazole (5.0 g, 0.031 mol) was dissolved in THF (25 mL) and the solution was slowly added to the solution prepared. Iodomethane (2.48 mL, 0.040 mol) was slowly added to the mixed solution at the same temperature, followed by stirring for 2 hours. The reaction solution was concentrated under reduced pressure, and added with water and ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrated compound (1-methyl added (Rf=0.8):2-methyl added (Rf=0.3)=1:1) was purified using silica gel chromatography (ethyl acetate:hexane=1:1 (v/v)) to obtain the title compound (Rf=0.8, 2.22 g, 41%).

Workup

  1. additionthe solution was slowly added to the solution
  2. customprepared
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionadded with water and ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionThe concentrated compound (1-methyl added (Rf=0.8):2-methyl added (Rf=0.3)=1:1)
  9. customwas purified

Sources & evidence

ORD record
ord-805f158b89714ede9b8d9e65766c90a9
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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