2-Nitro-4-toluonitrile → 2-Amino-4-methylbenzonitrile

HRID 442962

Reaction equation

HRID 442962 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N+:10]([O-])=O)[CH:3]=1>[Pd].O1CCOCC1>[NH2:10][C:4]1[CH:3]=[C:2]([CH3:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 1

HCID 962352-Nitro-4-toluonitrile

Product 1

HCID 28012762-Amino-4-methylbenzonitrileYield 83.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-methyl-2-nitrobenzonitrile (4.9 g, 30 mmol) and 10% palladium on carbon (500 mg) in 1,4-dioxane (60 mL) was stirred under hydrogen (balloon) overnight. The catalyst was removed by filtration through the Celite, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (dichloromethane) to give the title compound as a pale yellow solid (3.3 g, 83%). 1H-NMR (300 MHz, CDCl3) δ 7.26 (d, J=8.3 Hz, 1H), 6.56 (s, 1H), 6.55 (s, 1H), 4.32 (br s, 2H), 2.29 (s, 3H).

Workup

  1. customThe catalyst was removed by filtration through the Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography (dichloromethane)

Sources & evidence

ORD record
ord-9cfd7fd935834a369adcceeb8e01b05c
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Linked notes

Loading…