Acetic Acid → 2,6-Diethyl-4-nitroaniline

HRID 1657929Notes

Reaction equation

HRID 1657929 reaction equation
[CH3:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11]C(C)=O.C(O)(=O)C.S(=O)(=O)(O)O.[N+:24]([O-])([OH:26])=[O:25]>O>[CH2:2]([C:3]1[CH:8]=[C:7]([N+:24]([O-:26])=[O:25])[CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH2:11])[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 855342,6-Diethylacetanilide

Product 1

HCID 81426772,6-Diethyl-4-nitroaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 58 parts of 2,6-diethylacetanilide in 100 parts of glacial acetic acid and 184 parts of concentrated sulfuric acid is treated at 10° with a mixture of 19.5 parts by volume of concentrated nitric acid and 13 parts by volume of concentrated sulfuric acid. After addition is completed, the mixture is stirred at 25°C for 1 hour. It is then poured into water and ice, and the solid filtered, washed with water and dried. The 2,6-diethyl-4-nitroacetanilide (30 parts) is treated with 150 parts by volume of refluxing 70% sulfuric acid solution for one hour, and the mixture poured onto ice and made basic with 5N sodium hydroxide solution. The solid 2,6-diethyl-4-nitroaniline is filtered, washed with water and recrystallized from methyl alcohol-water.

Workup

  1. additionAfter addition
  2. filtrationthe solid filtered
  3. washwashed with water
  4. customdried
  5. additionThe 2,6-diethyl-4-nitroacetanilide (30 parts) is treated with 150 parts by volume
  6. temperatureof refluxing 70% sulfuric acid solution for one hour
  7. additionthe mixture poured onto ice
  8. filtrationThe solid 2,6-diethyl-4-nitroaniline is filtered
  9. washwashed with water
  10. customrecrystallized from methyl alcohol-water

Sources & evidence

ORD record
ord-b229c07cf431458fa47a34d1c433f267
Source dataset
uspto-grants-1976_06
Patent number
US03962307

Reaction notes

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