Nitric Acid → 2-Ethyl-5-nitroaniline

HRID 645674Notes

Reaction equation

HRID 645674 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].[N+:10]([O-])([OH:12])=[O:11].[OH-].[Na+]>OS(O)(=O)=O>[CH2:1]([C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 113572-EthylanilineHCID 14798Sodium Hydroxide

Product 1

HCID 41554782-Ethyl-5-nitroaniline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-ethylaniline (12.1 g, 0.1 mol) in conc. H2SO4 (50 mL) at 0° C. was added fuming HNO3 (9.3 g) drop wise. After stirring at ambient temperature for 30 min, the mixture was poured into ice-water, and 2 N NaOH was added to neutralize the excess acid. The resulting reddish-brown solid was collected by filtration and washed with petroleum ether to give 2-ethyl-5-nitroaniline as crude product (9 g).

Workup

  1. additionwas added
  2. filtrationThe resulting reddish-brown solid was collected by filtration
  3. washwashed with petroleum ether

Sources & evidence

ORD record
ord-b648a9244507480d9368c8894bdcb4c4
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

Loading…