Nitric Acid → 4-Chloro-2-methyl-5-nitroaniline

HRID 263822Notes

Reaction equation

HRID 263822 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[NH2:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 72514-Chloro-2-toluidine

Product 1

HCID 2929654-Chloro-2-methyl-5-nitroaniline

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

7 g (20 mmol) of 2-amino-5-chlorotoluene were dissolved in 10 ml of sulfuric acid at 10° C. to form a reactant solution. 2.05 ml fuming nitric acid were dissolved in 10 ml concentrated sulfuric acid and the resultant acidic solution was added slowly dropwise to the reactant solution. The reactant solution was then stirred for 3 to 4 hours at room temperature and subsequently added to ice. The yellow product crystals were filtered with suction and recrystallized from methanol. 6.4 g (70% of the theoretical yield) of 2-amino-5-chloro-4-nitrotoluene, which melted at 115° C., were obtained.

Workup

  1. customto form a reactant solution
  2. additionthe resultant acidic solution was added slowly dropwise to the reactant solution
  3. additionsubsequently added to ice
  4. filtrationThe yellow product crystals were filtered with suction
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9b5a8c1124274c03b660e1b2f36ca95e
Source dataset
uspto-grants-1997_07
Patent number
US05645610

Reaction notes

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