Nitric Acid → 4-Isopropyl-2-nitroaniline

HRID 461437Notes

Reaction equation

HRID 461437 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(OC(=O)C)(=O)C.[N+:18]([O-])([OH:20])=[O:19].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:18]([O-:20])=[O:19])[CH:5]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 74644-IsopropylanilineHCID 7918Acetic AnhydrideHCID 10340Sodium Carbonate

Product 1

HCID 27366964-Isopropyl-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

20.0 G. (0.148 moles) of 4-isopropylaniline is added with stirring to 75 ml. of acetic anhydride at from 20° to 45° C. The reaction mixture is stirred at 35° C. for 1 hour. 11 Ml. of fuming nitric acid (specific gravity 1.5) is added at a temperature of from 25° to 35° C. over a period of 20 minutes and stirred for 3 hours. The acid mixture is added to a mixture of 180 ml. of water, 45 ml. of concentrated sulfuric acid and 142 ml. of ethanol with stirring. The reaction mixture is stirred overnight at room temperature, refluxed for 2 hours, neutralized with saturated sodium carbonate solution and extracted with chloroform. The chloroform layer is dried and evaporated in vacuo affording 35 g. of a dark orange oil which is used as is in the next step.

Workup

  1. customat from 20° to 45° C
  2. stirringThe reaction mixture is stirred at 35° C. for 1 hour
  3. stirringstirred for 3 hours
  4. additionThe acid mixture is added to a mixture of 180 ml
  5. stirringThe reaction mixture is stirred overnight at room temperature
  6. temperaturerefluxed for 2 hours
  7. extractionextracted with chloroform
  8. dry with materialThe chloroform layer is dried
  9. customevaporated in vacuo
  10. customaffording 35 g

Sources & evidence

ORD record
ord-81b3409ab61e47ba89d0c891765661f4
Source dataset
uspto-grants-1977_12
Patent number
US04062952

Reaction notes

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