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

HRID 855633Notes

Reaction equation

HRID 855633 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-f22762afff4c47e193bf7af16fd40617
Source dataset
uspto-grants-2007_08
Patent number
US07262203B2

Reaction notes

Loading…