Nitric Acid → 2,4-Dimethylnitrophenylamine

HRID 1869403Notes

Reaction equation

HRID 1869403 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[N+:10]([O-])([OH:12])=[O:11].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH:4][N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 72502,4-DimethylanilineHCID 14798Sodium Hydroxide

Product 1

HCID 179891122,4-DimethylnitrophenylamineYield 95%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
4 °C

Procedure

In a solution that consists of 2,4-dimethylaniline (12.4 ml, 100 mmol) in 80 ml of concentrated sulfuric acid, it is mixed at 0° C. with 5.0 ml of fuming nitric acid and stirred for 20 minutes at 4° C., and then for 30 minutes at room temperature. The reaction mixture is poured into 600 ml of ice water, and set at a pH of 10 with 5N sodium hydroxide solution. The precipitate is suctioned off, washed with water and dried. 15.72 g (95% of theory) of 2,4-dimethylnitrophenylamine is obtained as a mixture of regioisomers.

Workup

  1. waitfor 30 minutes at room temperature
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-c2b61a7505e94a0fac2cfbb5c1e4d845
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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