3-Nitrophenylethyl alcohol → 2-(3-Aminophenyl)ethan-1-ol

HRID 1614930Notes

Reaction equation

HRID 1614930 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 1040583-Nitrophenylethyl alcohol

Product 1

HCID 149389872-(3-Aminophenyl)ethan-1-olYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a pressure bottle were added 2-(3-nitrophenyl)ethanol (3.0 g, 18 mmol) and methanol (100 mL) and 10% palladium on carbon (0.1 g, 0.08 mmol). The reaction mixture was hydrogenated at 45 psi overnight. The resultant mixture was filtered and concentrated to provide the desired product (2.44 g, 99%) as a white solid. LCMS for C8H12NO (M+H)+: m/z=138.1.

Workup

  1. customwas hydrogenated at 45 psi overnight
  2. filtrationThe resultant mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-24c2269c38e84f4aa6d1111c1263adb6
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

Loading…