Water → 1H-Indazol-3-ylmethanol

HRID 2182335

Reaction equation

HRID 2182335 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16](OC)=[O:17])=[N:8]1.O>O1CCCC1.[OH-].[Na+]>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][OH:17])=[N:8]1

Participants

6

Reactant 3

HCID 962Water2×HCID 657476methyl 1H-indazole-3-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 1785200261H-Indazol-3-ylmethanolYield 52.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

3.2 g of lithium aluminium hydride are added portionwise to a solution of 7.08 g of methyl 3-indazolecarboxylate in 80 ml of tetrahydrofuran, cooled to a temperature in the region of 0° C. by an ice bath. After 4 hours at a temperature in the region of 0° C., 1.6 g of lithium aluminium hydride are added. After 2 hours at a temperature in the region of 0° C., the reaction medium is treated successively with 6 ml of water and then 6 ml of aqueous IN sodium hydroxide solution and finally 18 ml of water. The reaction mixture is filtered through paper and the aqueous filtrate is then extracted with dichloromethane. The collected organic fractions are combined, dried over magnesium sulphate and concentrated under reduced pressure at a temperature in the region of 40° C. 3.15 g of (1H-indazol-3-yl)methanol are obtained in the form of an off-white powder, the characteristics of which are as follows:

Workup

  1. filtrationThe reaction mixture is filtered through paper
  2. extractionthe aqueous filtrate is then extracted with dichloromethane
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-a1f7c8d8716f419595b3ba3f83694173
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Linked notes

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