Sodium borohydride → (6-methyl-1H-indol-3-yl)methanamine

HRID 646064Notes

Reaction equation

HRID 646064 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[N:12]O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][NH2:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1363955696-Methyl-1H-indole-3-carbaldehyde oxime

Product 1

HCID 28806263(6-methyl-1H-indol-3-yl)methanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 6-methyl-1H-indole-3-carbaldehyde oxime (0.66 g) and NiCl2.6H2O (0.97 g) in methanol (60 ml) was added at 22° C. sodium borohydride (3.04 g) in portions. The suspension was filtered and the filtrate evaporated. The residue was partitioned between aqueous NH3 (1%) and ethyl acetate, the organic layer was dried and evaporated to the give crude C-(6-methyl-1H-indol-3-yl)-methylamine as a yellow semi solid (0.68 g).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between aqueous NH3 (1%) and ethyl acetate
  4. customthe organic layer was dried
  5. customevaporated to the

Sources & evidence

ORD record
ord-ff46ffc93f7c49d1a10531bae6821198
Source dataset
uspto-grants-2010_04
Patent number
US07705034B2

Reaction notes

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