2-Methyl-4-methoxyaniline → 5-Methoxy-1H-indazole

HRID 1269710

Reaction equation

HRID 1269710 reaction equation
[N:1]([O-])=O.[Na+].[CH3:5][O:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([CH3:14])[CH:8]=1>O.C(O)(=O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:10](=[CH:12][CH:13]=1)[NH:11][N:1]=[CH:14]2

Participants

5

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 133468605-Methoxy-1H-indazoleYield 18%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of sodium nitrite (3.38 g, 49.0 mmol) in water (8.1 ml) was added to a solution of 4-methoxy-2-methylaniline (6.69 g, 48.8 mmol) in acetic acid (350 ml) in an ice-water bath while maintaining the temperature at 25° C. or lower, and stirred overnight at room temperature. Then, the reaction solution was poured into water and extracted with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=9/1) to obtain 5-methoxy-1H-indazole (1.30 g, 18%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-b7b0052466d34fc48cbc3686dba485bc
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Linked notes

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