Nitric Acid → 4-Ethyl-2-nitroaniline

HRID 986666Notes

Reaction equation

HRID 986666 reaction equation
NC1C([N+:8]([O-:10])=[O:9])=CC=CC=1C.[CH2:12]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)[CH3:13].[N+]([O-])(O)=O>C(OC(=O)C)(=O)C>[CH2:12]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[C:16]([N+:8]([O-:10])=[O:9])[CH:15]=1)[CH3:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 112982-Methyl-6-nitroanilineHCID 115044-Ethylaniline

Product 1

HCID 2516744-Ethyl-2-nitroanilineYield 69.32%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

According to the method of synthesis for 2-amino-3-nitrotoluene (Organic Syntheses Collective Volume IV P.42-45) 6 g of 4- ethylaniline was added dropwise to 30 ml of acetic anhydride and then, the mixture was treated dropwise with 6.3 ml (100 m mol) of 70% nitric acid at 12°-13° C. After the mixture was stirred for some time at 10°-12° C., the reaction solution was poured into an ice water. Oily product was separated and heated with 15 ml of concentrated hydrochloric for one hour. The reaction solution was alkaline with dilute aqueous sodium hydroxide and then, partitioned with 100 ml of chloroform. The organic layer was washed with water and dried on anhydrous sodium sulfate. Removal of the solvent in vacuo gave 5.76 g (69.32%) of 4-ethyl-2-nitroaniline.

Workup

  1. customOily product was separated
  2. temperatureheated with 15 ml of concentrated hydrochloric for one hour
  3. custompartitioned with 100 ml of chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried on anhydrous sodium sulfate
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-8cfce940d5b543a8a4fc51c1d13ba2a3
Source dataset
uspto-grants-1987_12
Patent number
US04714764

Reaction notes

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