Chloride → 2,6-Dichloro-3-methylaniline

HRID 974410Notes

Reaction equation

HRID 974410 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10]C(=O)C.O.C(O)CC.[Cl-]>Cl.CC(O)=O>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH2:10]

Participants

7

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 10311-PropanolHCID 87254Acetamide, N-(2,6-dichloro-3-methylphenyl)-

Product 1

HCID 1165292,6-Dichloro-3-methylanilineYield 90.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

N-(2,6-Dichloro-3-methylphenyl)acetamide (22 g) was suspended in HCl (5.0 N, 100 mL), H2O (300 mL) and propanol (or AcOH, 20-50 mL). The mixture was refluxed for several hr after which the solution was cooled, chloride (3×200 mL). The organic extractions were combined, washed with water, dried over MgSP4, and concentrated to give 16 g of product as a low melting solid (m.p. 36°-38° C.). 1H NMR (CCl4) δ6.97 (d, 9.0), 6.46 (d, 9.0 Hz, 1H), 2.28 (s, 3H, CH3)

Workup

  1. temperatureThe mixture was refluxed for several hr after which the solution
  2. temperaturewas cooled
  3. extractionThe organic extractions
  4. washwashed with water
  5. dry with materialdried over MgSP4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b6dc76355844f379923200df65b06f4
Source dataset
uspto-grants-1991_11
Patent number
US05068392

Reaction notes

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