1,3-Dimethyl-5-nitrobenzene → 3,5-Dimethylaniline

HRID 1514873Notes

Reaction equation

HRID 1514873 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:11])[CH:7]=[C:8]([CH3:10])[CH:9]=1)([O-])=O>CO.[Pd]>[CH3:10][C:8]1[CH:9]=[C:4]([NH2:1])[CH:5]=[C:6]([CH3:11])[CH:7]=1

Participants

4

Reactant 1

HCID 74261,3-Dimethyl-5-nitrobenzene

Product 1

HCID 79493,5-Dimethylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5-nitro-m-xylene (1.51 g) and 10% Pd/C (80 mg) in MeOH (50 mL) was stirred at room temperature under H2 balloon for 16 h. The reaction mixture was filtered through a Celite pad, washed with EtOAc, concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=5:95 to 40:60) to give 3,5-dimethyl-phenylamine as a yellow oil: MS (m/z) 122 (M+1); 1H NMR (CDCl3, 400 MHz) δ 6.41 (s, 1H), 6.33 (s, 2H), 3.52 (s, 2H), 2.22 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. washwashed with EtOAc
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=5:95 to 40:60)

Sources & evidence

ORD record
ord-589d38271f6d444fbd1d6d4579de881d
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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