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

HRID 2075427Notes

Reaction equation

HRID 2075427 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-8acd899441a34927b8dade6c100ef8f8
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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