Ethyl Acetate → N-(2-chloro-5-nitrophenyl)-4-methylbenzamide

HRID 1896774

Reaction equation

HRID 1896774 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[CH3:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.C(OCC)(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH:4][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([CH3:12])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 134054-Methylbenzoyl ChlorideHCID 226912-Chloro-5-nitroaniline

Product 1

HCID 3330399N-(2-chloro-5-nitrophenyl)-4-methylbenzamideYield 42%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To 2-chloro-5-nitroaniline (2 g, 11.59 mmol) in pyridine (5 mL) at room temperature was added 4-methylbenzoyl chloride (1.6 mL, 12.17 mmol), followed by pyridine (5 mL). The mixture was then stirred at room temperature for 16 h. Ethyl acetate was then added to the solution to give a precipitate, which was filtered off and washed twice with ethyl acetate, and then hexanes. The resulting solid was then washed with aqueous sodium bicarbonate, 1M aqueous sodium hydroxide, water and hexanes to afford (1.4 g, 42%) of the title compound.

Workup

  1. customto give a precipitate, which
  2. filtrationwas filtered off
  3. washwashed twice with ethyl acetate
  4. washThe resulting solid was then washed with aqueous sodium bicarbonate, 1M aqueous sodium hydroxide, water and hexanes

Sources & evidence

ORD record
ord-d81dff55bf5c4ca1882e75664806ad58
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Linked notes

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