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

HRID 1640712Notes

Reaction equation

HRID 1640712 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-99457dff5fa54a50859399329c9ece5c
Source dataset
uspto-grants-2012_02
Patent number
US08114885B2

Reaction notes

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