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

HRID 1432500Notes

Reaction equation

HRID 1432500 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.O.[BH4-].[Na+]>CO.Cl[Ni]Cl>[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

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 1363955696-Methyl-1H-indole-3-carbaldehyde oxime

Product 1

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

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 6-methyl-1H-indole-3-carbaldehyde oxime (0.66 g) and NiCl2.6 H2O (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 the crude title compound 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-bd97439874cc48018494efd13396b43c
Source dataset
uspto-grants-2009_11
Patent number
US07612099B2

Reaction notes

Loading…