Hydrochloric Acid → 6-Nitro-2,4-xylidine

HRID 1466481Notes

Reaction equation

HRID 1466481 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].Cl>C(OC(=O)C)(=O)C>[CH3:9][C:7]1[CH:8]=[C:2]([CH3:1])[C:3]([NH2:4])=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 72502,4-Dimethylaniline

Product 1

HCID 742196-Nitro-2,4-xylidineYield 97%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2,4-Dimethylaniline (8.0 g, 66.0 mmol) was dissolved in acetic anhydride (50 mL), and nitric acid (5 mL) was slowly added in drops thereto at 0° C. After stirring for 30 min, the mixture was diluted with ice water (200 mL). Conc. hydrochloric acid (10 mL) was added in drops thereto, and the resulting mixture was stirred under reflux for 4 h. After the reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure. The residue was diluted with aqueous ammonium hydroxide solution. The resulting orange solid was filtered and dried to give the title compound (10.6 g, Yield 97%).

Workup

  1. customat 0° C
  2. stirringthe resulting mixture was stirred
  3. temperatureunder reflux for 4 h
  4. customthe solvent was removed under reduced pressure
  5. additionThe residue was diluted with aqueous ammonium hydroxide solution
  6. filtrationThe resulting orange solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-a19f7796e34c471681777bb637f0c174
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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