3-(4-Nitrophenyl)prop-2-en-1-ol → 4-Aminobenzenepropanol

HRID 2293410Notes

Reaction equation

HRID 2293410 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]=[CH:9][CH2:10][OH:11])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 739253-(4-Nitrophenyl)prop-2-en-1-ol

Product 1

HCID 2204244-Aminobenzenepropanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
22 °C

Procedure

To a round bottomed flask equipped with a magnetic stirrer was added 4-nitrocinnamyl alcohol (2.0 g, 11.16 mmol), 10% Pd on carbon (200 mg) and absolute ethanol (150 mL). The solution was purged with hydrogen and stirred at 22° C. under a hydrogen atmosphere. When TLC indicated the reaction was complete (4 hr), the solution was purged with argon and filtered through Celite. The filtrate was concentrated in vacuo to provide 3-(4-aminophenyl)propanol, 1.72 g (>100%), as a viscous oil which solidified on standing.

Workup

  1. customTo a round bottomed flask equipped with a magnetic stirrer
  2. customThe solution was purged with hydrogen
  3. custom(4 hr)
  4. customthe solution was purged with argon
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e517594663a9405f9aeb74e7f9c862b3
Source dataset
uspto-grants-1997_11
Patent number
US05686424

Reaction notes

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