Methyl 3-(1-azidoethyl)benzoate → Methyl 3-(1-aminoethyl)benzoate

HRID 2238656Notes

Reaction equation

HRID 2238656 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([N:12]=[N+]=[N-])[CH3:11])[CH:5]=1.[H][H]>C(O)C.[C].[Pd]>[NH2:12][CH:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:15])[CH3:11]

Participants

5

Reactant 2

HCID 86227459Methyl 3-(1-azidoethyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 19933442Methyl 3-(1-aminoethyl)benzoateYield 57.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

600 mg of the methyl 3-(1-azidoethyl)benzoate [100-1] was dissolved in 15 mL of ethanol, 200 mg of 10% palladiumcarbon catalyst was added thereto, and stirred overnight in a hydrogen atmosphere. The insolubles were filtered through celite, washed with ethanol, and then the filtrate was concentrated under reduced pressure to obtain 300 mg of methyl 3-(1-aminoethyl)benzoate [100-2] as a colorless oily product.

Workup

  1. filtrationThe insolubles were filtered through celite
  2. washwashed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b990d1d4cd3c4df8b735c8b870db8e00
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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