Water → 1-Methyl-4-nitro-1H-indazole

HRID 586072

Reaction equation

HRID 586072 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[N:9][NH:10]2)([O-:5])=[O:4].[CH3:15]I.O>CN(C=O)C>[CH3:15][N:10]1[C:11]2[C:7](=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=[CH:13][CH:12]=2)[CH:8]=[N:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 180574-NitroindazoleHCID 24758Sodium hydride

Product 1

HCID 2802131-Methyl-4-nitro-1H-indazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A suspension of NaH (1.1 g, 32.2 mmol; 60% dispersion in mineral oil) in DMF (40 mL) was treated with 4-nitro-1H-indazole (5 g, 30.6 mmol) in DMF (40 mL) at 0° C. After stirring for 30 minutes, the mixture was treated with methyl iodide (4.6 g, 32.18 mmol) in DMF (20 ml) drop wise. The mixture was allowed to gradually warm to ambient temperature and stir overnight. The mixture was poured into water (250 ml) and extracted with ethyl acetate (2×100 mL). The organics were combined, washed with water, brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was chromatographed (SiO2, ethyl acetate/hexanes) to provide the title compound. 1H NMR (DMSO-d6) δ 8.50 (s, 1H), 8.24 (d, 1H), 8.19 (d, 1H), 7.65 (t, 1H).

Workup

  1. stirringstir overnight
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was chromatographed (SiO2, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-20db3f0d822d4d408ae7611a7ad968f2
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Linked notes

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