Ammonia → 5-(Aminomethyl)-1H-indazole

HRID 2088981Notes

Reaction equation

HRID 2088981 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.N.[H][H]>C1COCC1.CO.[Ni]>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 111263841H-Indazole-5-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 120962235-(Aminomethyl)-1H-indazole

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1H-indazole-5-carbonitrile (0.235 g, 1.64 mmol) in THF (6 mL) was added 2 mL of 2 N ammonia in methanol and the flask was charged with 0.05 g Raney® 2800 nickel. A hydrogen balloon was attached to the flask and the system was purged 3 times with hydrogen. After stirring vigorously overnight the reaction mixture was diluted with methanol and filtered through a pad of celite. The solvent was evaporated in vacuo to provide 1-(1H-indazole-5-yl)methanamine.

Workup

  1. customthe system was purged 3 times with hydrogen
  2. additionwas diluted with methanol
  3. filtrationfiltered through a pad of celite
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1219f384a4d142bdb185821b5e1b19a3
Source dataset
uspto-grants-2013_05
Patent number
US08436016B2

Reaction notes

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