Nitric Acid → Ethanone, 1-(5-amino-2-nitrophenyl)-

HRID 1662940

Reaction equation

HRID 1662940 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10]C(=O)C(F)(F)F)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[N+:17]([O-])([OH:19])=[O:18]>OS(O)(=O)=O>[C:1]([C:4]1[CH:5]=[C:6]([NH2:10])[CH:7]=[CH:8][C:9]=1[N+:17]([O-:19])=[O:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 673706Acetanilide, 3'-acetyl-2,2,2-trifluoro-

Product 1

HCID 6420386Ethanone, 1-(5-amino-2-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The starting material, about 10 mmol of 3-acetyl-trifluoroacetylaminobenzene was gradually added to about 20 ml of concentrated H2SO4 at about −20° C., and then stirred for about 30 minutes. Then, nitric acid was added for about 10 minutes. The solution was stirred for about 2 hours. After the reaction was completed, the solution was poured into ice water. An organic layer was extracted twice from the ice water with about 50 mL ethyl acetate, and was washed with sodium hydrogen carbonate solution. And then the organic layer was dried with sodium sulfate anhydride, and distilled under reduced pressure to remove ethyl acetoacetate. Concentrated NH4OH was added, and the solution was stirred at about 50° C. for about 1 hour. Then, the solution was evaporated using a rotary. Extraction was performed with EtOAc and water. Then, 3-acetyl-4-nitro-aminobenzene was obtained in a form of about 54% brown solid using silica gel column chromatography (Hexane/EtOAc=3/1).

Workup

  1. stirringThe solution was stirred for about 2 hours
  2. extractionAn organic layer was extracted twice from the ice water with about 50 mL ethyl acetate
  3. washwas washed with sodium hydrogen carbonate solution
  4. dry with materialAnd then the organic layer was dried with sodium sulfate anhydride
  5. distillationdistilled under reduced pressure
  6. customto remove ethyl acetoacetate
  7. additionConcentrated NH4OH was added
  8. stirringthe solution was stirred at about 50° C. for about 1 hour
  9. customThen, the solution was evaporated
  10. extractionExtraction

Sources & evidence

ORD record
ord-80720b4f73db4bda915b8df5ae2a7c76
Source dataset
uspto-grants-2011_10
Patent number
US08034747B2

Linked notes

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