Sodium Hydroxide → (2-methyl-6-nitro-2H-indazol-3-yl)methanol

HRID 2265872Notes

Reaction equation

HRID 2265872 reaction equation
Br[CH2:2][C:3]1[N:4]([CH3:15])[N:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7]2.[OH-:16].[Na+]>CC#N.O>[CH3:15][N:4]1[C:3]([CH2:2][OH:16])=[C:11]2[C:6]([CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:10]2)=[N:5]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 219563503-(bromomethyl)-2-methyl-6-nitro-2H-indazole

Product 1

HCID 21956359(2-methyl-6-nitro-2H-indazol-3-yl)methanolYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

3-(Bromomethyl)-2-methyl-6-nitro-2H-indazole (4.20 g, ˜14.9 mmol) in CH3CN (500 ml) and water (200 ml) was treated with NaOH to give pH˜11. The solution was stirred at rt for 2 days then conc. in vacuo and repeatedly extracted with dichloromethane and chloroform. The combined organic extracts were evaporated, and the crude product was purified by silica gel column chromatography to give (2-methyl-6-nitro-2H-indazol-3-yl)methanol (1.03 g, 33% TY). MS (ES+, m/z) 208.

Workup

  1. customto give pH˜11
  2. extractionconc. in vacuo and repeatedly extracted with dichloromethane and chloroform
  3. customThe combined organic extracts were evaporated
  4. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e9bc7907d3f64491a47e0ec6e422c76d
Source dataset
uspto-grants-2010_12
Patent number
US07858626B2

Reaction notes

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