Water → 1H-Indazol-3-ylmethanol

HRID 2064572

Reaction equation

HRID 2064572 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.[OH-].[Na+]>O1CCCC1>[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 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 657476methyl 1H-indazole-3-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 1785200261H-Indazol-3-ylmethanolYield 52.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 1N 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-3e39270afb724279aeeeeb1481fd2370
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Linked notes

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