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

HRID 1955144Notes

Reaction equation

HRID 1955144 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 113692,6-Diethylaniline

Product 1

HCID 81426772,6-Diethyl-4-nitroaniline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 2,6-diethylaniline (5.0 g, 34 mmol) in concentrated sulfuric acid (30 mL) at 0° C. was added dropwise concentrated nitric acid (15.9M, 2.10 mL, 34 mmol). The cooling bath was removed, and the reaction was stirred for 3 hours at ambient temperature. After pouring the reaction mixture into ice, the solution was neutralized using 4N sodium hydroxide and extracted with methylene chloride (3×50 mL). The extracts were dried with sodium sulfate, and solvents were removed in vacuo to give the title compound.

Workup

  1. customThe cooling bath was removed
  2. additionAfter pouring the reaction mixture into ice
  3. extractionextracted with methylene chloride (3×50 mL)
  4. dry with materialThe extracts were dried with sodium sulfate, and solvents
  5. customwere removed in vacuo

Sources & evidence

ORD record
ord-d24e8f078ae04f69ab99f3b1689f6156
Source dataset
uspto-grants-2000_09
Patent number
US06124341

Reaction notes

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