Ammonium Chloride → (1-tosyl-1H-indol-6-yl)methanamine

HRID 475055Notes

Reaction equation

HRID 475055 reaction equation
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([CH:20]=O)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH4+:22].[Cl-]>CCO.[Zn]>[S:1]([N:11]1[C:19]2[C:18](=[CH:17][CH:16]=[C:15]([CH2:20][NH2:22])[CH:14]=2)[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 131150931-Tosyl-1H-indole-4-carbaldehyde

Product 1

HCID 71272360(1-tosyl-1H-indol-6-yl)methanamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

4-Aminomethylindole, 5-aminomethylindole and 6-aminomethylindole are known compounds. It is sometimes convenient to protect the indole nitrogen and in those instances a tosyl group was first introduced. 1-Tosyl-1H-indole-6-carbonitrile (CASRN31274-87-1) was reduced with H2 and RaNi in 7N ammonical methanol to afford the corresponding aminomethyl derivative. 1-Tosyl-1H-indole-4-carbaldehyde was converted to the oxime and reduced with Zn and NH4Cl in EtOH to afford (1-tosyl-1H-indol-6-yl)methanamine.

Sources & evidence

ORD record
ord-4fc9ed0dd06c4fe48cbc4956a9a9cb16
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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