Nitric Acid → 4-(Ethylamino)-3-nitrobenzonitrile

HRID 1356699Notes

Reaction equation

HRID 1356699 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([N:7]([CH2:18][CH3:19])S(C2C=CC(C)=CC=2)(=O)=O)=[CH:5][CH:4]=1)#[N:2].[N+:22]([O-])([OH:24])=[O:23]>S(=O)(=O)(O)O>[C:1]([C:3]1[CH:21]=[CH:20][C:6]([NH:7][CH2:18][CH3:19])=[C:5]([N+:22]([O-:24])=[O:23])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 185093134'-Cyano-N-ethyl-p-toluenesulfonanilide

Product 1

HCID 31180704-(Ethylamino)-3-nitrobenzonitrileYield 28%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4′-Cyano-N-ethyl-p-toluenesulfonanilide (6.95 g (23.1 mmol) was dissolved in concentrated sulfuric acid (20.0 ml) under cooling with ice. To this, 97% fuming nitric acid (1.00 ml (23.4 mmol)) was added dropwise and the mixture was stirred for 30 minutes under cooling with ice. The resulting mixture was poured into ice-water, followed by extraction with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with ethyl acetate-hexane (1:3) as eluent, to give 1.25 g (28%) of 4-cyano-N-ethyl-2-nitroaniline as yellow crystals.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b153892e567c41bb87388a3462656afe
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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