Benzene, 4-chloro-1-methyl-2-nitro- → 5-Chloro-2-methylaniline

HRID 451692

Reaktionsgleichung

Reaktionsgleichung von HRID 451692
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1>CO.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([NH2:9])[CH:3]=1

Komponenten

4

Edukt 1

HCID 6975Benzene, 4-chloro-1-methyl-2-nitro-

Produkt 1

HCID 72605-Chloro-2-methylanilineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A 2 L flask was charged the solution of 4-chloro-1-methyl-2-nitrobenzene (60 g, 0.35 mol) in MeOH (1 L), Raney Ni was added, the air in flask was replaced three times with H2, the mixture was stirred for 3 h at rt. The solution was filtered and concentrated. The residue was dissolved in CH2Cl2 (500 mL), and the solution was washed with brine, dried over Na2SO4. Solvent removal gave 5-chloro-2-methylbenzenamine (50 g, 0.35 mol). 1H NMR (CDCl3, 400 MHz) δ 7.02-6.93 (d, 2H), 6.70-6.60 (d, 2H), 3.67 (s, 2H), 2.14 (s, 3H).

Aufarbeitung

  1. additionwas added
  2. customthe air in flask was replaced
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2 (500 mL)
  6. washthe solution was washed with brine
  7. dry with materialdried over Na2SO4
  8. customSolvent removal

Quellen und Nachweise

ORD-Eintrag
ord-2c976f0513b1424aa151dd74b1054d77
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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