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

HRID 218395

Reaction equation

HRID 218395 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 hr 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-22fab2f8201343bba2bda214ce1fd444
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Linked notes

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