3-(3-Nitrophenyl)propan-1-ol → 3-(3-Aminophenyl)propan-1-ol

HRID 1614960Notes

Reaction equation

HRID 1614960 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 113328423-(3-Nitrophenyl)propan-1-ol

Product 1

HCID 101033343-(3-Aminophenyl)propan-1-olYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(3-nitrophenyl)propan-1-ol (2.70 g, 14.9 mmol) in methanol (50.0 mL) was added 10% palladium on carbon (0.54 g, 0.46 mmol). The resultant mixture was hydrogenated at 50 psi overnight. The reaction mixture was then filtered and concentrated to give the desired product as a light brown thick oil (2.16 g, 96%). LCMS for C9H14NO (M+H)+: m/z=152.1.

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-669d9eae962a486484393edba85a8bf2
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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