4-Methoxy-3-(4-methoxyphenyl)benzylazide → 4-Methoxy-3-(4-methoxyphenyl)benzylamine

HRID 2113116Notes

Reaction equation

HRID 2113116 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][N:8]=[N+]=[N-])=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][NH2:8])=[CH:5][C:4]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 223912444-Methoxy-3-(4-methoxyphenyl)benzylazide

Product 1

HCID 223912104-Methoxy-3-(4-methoxyphenyl)benzylamineYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-methoxy-3-(4-methoxyphenyl)benzylazide (0.82 g, 3.07 mmol) in ethanol (50 mL) was hydrogenated under atmospheric pressure for 16 hours. The catalyst was filtered off, the solvent removed under reduced pressure and the crude purified by column chromatography (hexane/ethyl acetate 6/1) to afford 400 mg of title compound.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customthe crude purified by column chromatography (hexane/ethyl acetate 6/1)

Sources & evidence

ORD record
ord-4187fc070e2640e8be743fe232a4c2e7
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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