N-(3-Chloro-4-cyano-2-methylphenyl)acetamide → 4-Amino-2-chloro-3-methylbenzonitrile

HRID 2171592Notes

Reaction equation

HRID 2171592 reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([NH:10]C(=O)C)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]>Cl.CCO>[NH2:10][C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[C:3]=1[CH3:14]

Participants

3

Reactant 1

HCID 58932655N-(3-Chloro-4-cyano-2-methylphenyl)acetamide

Product 1

HCID 218754134-Amino-2-chloro-3-methylbenzonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

A solution of N-(3-chloro-4-cyano-2-methylphenyl)acetamide (25 g, 0.119 mol) in 250 mL of concentrated HCl/EtOH (1:1) was refluxed 2 hrs. The EtOH was concentrated and ethyl acetate was added to the residue and the aqueous layer was neutralized with addition of saturated NaHCO3 solution. The organic layer was separated and dried over Na2SO4 and concentrated to give the crude aniline which was further purified by column chromatography using DCM as a solvent to yield the title compound (11.8 g, 60%).

Workup

  1. concentrationThe EtOH was concentrated
  2. additionethyl acetate was added to the residue
  3. additionthe aqueous layer was neutralized with addition of saturated NaHCO3 solution
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give the crude aniline which
  8. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-db7f692822ed4eaf98e16472643b08bb
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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