Sodium Hydroxide → 4,5-Dichloro-2-methylaniline

HRID 842927

Reaction equation

HRID 842927 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-])=O)=[C:4]([CH3:12])[CH:3]=1.[OH-].[Na+]>[Cl-].[Cl-].[Cl-].[Ti+3]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzene

Product 1

HCID 3437964,5-Dichloro-2-methylanilineYield 56.1%

Reagents, catalysts & solvents 1

HCID 10313229titanium(III) trichlorideSolvent

Procedure

4,5-Dichloro-2-methyl-nitrobenzene 5 (5.0 g, 24.3 mmol) was heated at 100° C. in titanium trichloride (30% in aqueous hdyrochloric acid, 25 mL) for 2 hrs., cooled to RT, the reaction solution was basified to pH 8 with 50% aqueous sodium hydroxide, then extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography using 10% ethyl acetate in hexanes to give 2.4 g (56%) of the title product. 1H NMR (400 MHz, CDCl3) δ7.09 (s, 1 H, Ar), 6.74 (s , 1 H, Ar), 3.63 (s, 2 H, NH2), 2.10 (s, 3H, CH3).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b3fff543e149441391bab4be31b9db1a
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Linked notes

Loading…