3-Hydroxy-3-(3-nitrophenyl)propanenitrile → 3-(3-Aminophenyl)-3-hydroxypropanenitrile

HRID 716747Notes

Reaction equation

HRID 716747 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)[CH2:3][C:4]#[N:5]>CCOC(C)=O.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]([CH:2]([OH:1])[CH2:3][C:4]#[N:5])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 593169073-Hydroxy-3-(3-nitrophenyl)propanenitrile

Product 1

HCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-hydroxy-3-(3-nitrophenyl)propanenitrile (11) (400 mg, 2.1 mmol) and Pd/C (20 mg, 10%) in EtOAc (15 ml) was degassed vacuum/hydrogen and then stirred at room temperature under H2 (balloon) for 15 hours. The mixture was filtered to remove the Pd/C and then concentrated under reduced pressure to give 3-(3-aminophenyl)-3-hydroxypropanenitrile (12) as while solid. Yield (390 mg, 99%). 1H NMR (400 MHz, CDCl3) δ 7.15 (t, J=8.0 Hz, 1H), 6.70-6.74 (m, 2H), 6.63-6.65 (m, 1H), 4.92 (t, J=6.0 Hz, 1H), 2.72 (d, J=6.0 Hz, 2H).

Workup

  1. customwas degassed vacuum/hydrogen
  2. filtrationThe mixture was filtered
  3. customto remove the Pd/C
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6f8696d86104e319572e5097451a4f1
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

Loading…