4-Chloro-2-nitroaniline → N-(4-chloro-2-nitrophenyl)acetamide

HRID 653047Notes

Reaction equation

HRID 653047 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1>S(=O)(=O)(O)O.O>[C:5]([NH:13][C:12]1[CH:14]=[CH:15][C:9]([Cl:8])=[CH:10][C:11]=1[N+:16]([O-:18])=[O:17])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 69794-Chloro-2-nitroanilineHCID 7918Acetic Anhydride

Product 1

HCID 2788431N-(4-chloro-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 50 ml of acetic anhydride and two drops of sulfuric acid was added 34.5 grams of 4-chloro-2-nitroaniline in several portions. At the end of addition, the solution was heated at 50° C. for one hour and then allowed to cool. 300 ml of cold water was added to the solution to induce precipitation of crystals, which were removed by filtration and washed with water. There were obtained the crystals of 2-acetylamino-5-chloronitrobenzene in a yield of 41.8 grams.

Workup

  1. additionAt the end of addition
  2. temperatureto cool
  3. customprecipitation of crystals, which
  4. customwere removed by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-4dec328e5bcd40e98eb823388ebab255
Source dataset
uspto-grants-1987_06
Patent number
US04675277

Reaction notes

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