Ethanol → HCID 22239012, compound

HRID 1711606Notes

Reaction equation

HRID 1711606 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][CH2:19][C:20]#[N:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.[CH2:25](O)[CH3:26]>[Ni]>[CH2:25]([NH:21][CH2:20][CH2:19][CH2:18][CH2:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[N:9]=1)[CH3:26]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 22239017HCID 22239017, compound

Product 1

HCID 22239012HCID 22239012, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
65 °C

Procedure

A solution of 1-benzyl-3-(3-cyanopropyl)indazole (100 mg, 0.35 mM) in ethanol (10 ml) was stirred at room temperature and Raney nickel (approx. 100 mg, wet weight) was added. The resulting suspension was warmed to 65° C. and hydrazine hydrate (0.1 ml, 87 mg) added carefully. The mixture was stirred at 70° C. for a further 2 hr then cooled and filtered through celite. Solvent was removed in vacuo and the residue purified by chromatography on silica (chloroform/methanol 9:1) to give the title product as a clear oil (25 mg, 26%).

Workup

  1. temperaturethen cooled
  2. filtrationfiltered through celite
  3. customSolvent was removed in vacuo
  4. customthe residue purified by chromatography on silica (chloroform/methanol 9:1)

Sources & evidence

ORD record
ord-7092103752d2415ab92785db08442ea3
Source dataset
uspto-grants-2010_09
Patent number
US07790761B2

Reaction notes

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