Hydrochloric Acid → 1-(1H-indol-6-yl)methanamine

HRID 2236431

Reaction equation

HRID 2236431 reaction equation
CO[N:3]=[CH:4][C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1.Cl>C(O)C.[Pd]>[NH:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([CH2:4][NH2:3])[CH:13]=2)[CH:9]=[CH:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 722508601H-Indole-6-carbaldehyde O-methyl-oxime

Product 1

HCID 172211011-(1H-indol-6-yl)methanamineYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An amount of 1H-Indole-6-carbaldehyde O-methyl-oxime (150 mg, 0.86 mmol) is dissolved in ethanol (6.5 mL). Then hydrogen chloride (0.62 mL) is added, followed by 10% Pd/C (15 mg). After hydrogenation at 35 psi for 3 h, the solution is filtered through Celite and evaporated to dryness. The residue is recrystallized from ethyl acetate to give 110 mg of crude product as a yellow solid. MS (ESI) m/z 147.3 (M+1).

Workup

  1. filtrationthe solution is filtered through Celite
  2. customevaporated to dryness
  3. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d95d069c5a3c43fcba9e0049620b2c2e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Linked notes

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