2-azido-1-(4-bromophenyl)ethanone → 2-Amino-1-(4-bromophenyl)ethanone

HRID 1943575Notes

Reaction equation

HRID 1943575 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)=[O:6])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 1

HCID 110210042-azido-1-(4-bromophenyl)ethanone

Product 1

HCID 216392-Amino-1-(4-bromophenyl)ethanoneYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 2-azido 4′-bromoacetophenone (1.0 g, 4.17 mmol) in MeOH (20 mL), Pd/C (10%, 100 mg) was added to the solution. The mixture was degassed and stirred under hydrogen system for 4 hours. The mixture was filtered and evaporated in vacuo without further purification to obtain 2-amino 4′-bromoacetophenone (0.535 g, 2.499 mmol, 60% yield). 1H NMR (d-MeOH) 4.63 (d, J=4.8 Hz, 2H), 7.62 (d, J=7.2 Hz, 2H), 8.03 (d, J=7.2 Hz, 2H) ppm.

Workup

  1. customThe mixture was degassed
  2. filtrationThe mixture was filtered
  3. customevaporated in vacuo without further purification

Sources & evidence

ORD record
ord-a439926c934c441b97dea3795376fc73
Source dataset
uspto-grants-2013_03
Patent number
US08394742B2

Reaction notes

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