Hydrochloric Acid → (1H-indol-4-yl)methanamine

HRID 2236435Notes

Reaction equation

HRID 2236435 reaction equation
CO[N:3]=[CH:4][C:5]1[C:6]2[CH:7]=[CH:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1.Cl>C(O)C.[Pd]>[NH:9]1[C:10]2[C:6](=[C:5]([CH2:4][NH2:3])[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 722508571H-Indole-4-carbaldehyde O-methyl-oxime

Product 1

HCID 280302(1H-indol-4-yl)methanamineYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An amount of 1H-Indole-4-carbaldehyde O-methyl-oxime (50 mg, 0.30 mmol) is dissolved in ethanol (5 mL). Then hydrogen chloride (0.217 mL) is added, followed by 10% Pd/C (5.0 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 42 mg of crude product as an orange residue. MS (ESI) m/z 147.2 (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-5c55b0ddf7ab4f5cac4df36e76f89fa2
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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