Hydrochloric Acid → 2,6-Dimethyl-4-nitroaniline

HRID 1820117

Reaction equation

HRID 1820117 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([CH3:12])[C:4]=1[NH:13]C(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([CH3:12])[C:4]=1[NH2:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 50851089N-(2,6-dimethyl-4-nitrophenyl)acetamide

Product 1

HCID 281592,6-Dimethyl-4-nitroanilineYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Concentrated hydrochloric acid (17.5 mL) was added to N-(2,6-dimethyl-4-nitro-phenyl)-acetamide (5.05 g) and heated to 140° C. for 30 minutes in a sealed microwave process vial. The reaction mixture was neutralized with solid sodium carbonate in water and the precipitated product was collected by filtration and washed with water (100 mL) to furnish 3.93 g (97% yield) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSO-d6): 2.15 (s, 6H), 6.15 (b, 2H), 7.79 (s, 2H).

Workup

  1. filtrationthe precipitated product was collected by filtration
  2. washwashed with water (100 mL)

Sources & evidence

ORD record
ord-6495e0fce7c44ab6b87b955008f683f2
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Linked notes

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