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

HRID 451692

Reaction equation

HRID 451692 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

HCID 72605-Chloro-2-methylanilineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2c976f0513b1424aa151dd74b1054d77
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Linked notes

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