Sodium sulfate decahydrate → (1H-Indazol-3-yl)-N,N-dimethylmethanamine

HRID 2378710Notes

Reaction equation

HRID 2378710 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:20])[C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][N:12]=1)=O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:20][N:8]([CH2:9][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][N:12]=1)[CH3:7]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 20816326N,N-Dimethyl-1H-indazole-3-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 178483331(1H-Indazol-3-yl)-N,N-dimethylmethanamineYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (13.7 g, 36.1 mmol) was suspended in THF (500 mL), and the suspension was added with a solution of N,N-dimethyl-1H-indazole-3-carboxamide obtained in Step 1 (34.2 g, 181 mmol) in THF (250 mL), followed by stirring at room temperature under the flow of nitrogen gas for 30 minutes. The reaction mixture was mixed with sodium sulfate decahydrate, was stirred for further 1 hour and was filtered through Celite. The solvent was evaporated under reduced pressure to obtain 3-dimethylaminomethyl-1H-indazole (24.2 g, 76%).

Workup

  1. stirringwas stirred for further 1 hour
  2. filtrationwas filtered through Celite
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-88d46f27265349149ee1bd6aa3e214e1
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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