Sulfuric Acid → Benzenamine, 3-ethoxy-4-nitro-

HRID 1935184Notes

Reaction equation

HRID 1935184 reaction equation
OS(O)(=O)=O.C([NH:9][C:10]1[CH:18]=[C:17]([O:19][CH2:20][CH3:21])[C:16]([N+:22]([O-:24])=[O:23])=[CH:15][C:11]=1C(O)=O)(=O)C.[OH-].[NH4+]>O>[CH2:20]([O:19][C:17]1[CH:18]=[C:10]([CH:11]=[CH:15][C:16]=1[N+:22]([O-:24])=[O:23])[NH2:9])[CH3:21]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 10308168HCID 10308168, compound

Product 1

HCID 11074030Benzenamine, 3-ethoxy-4-nitro-Yield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
111 °C

Procedure

To 600 ml of H2O was slowly added 400 ml conc. H2SO4. To the hot mixture was added 118.5 g 0.44 mol)) of 2-acetylamino-4-ethoxy-5-nitro-benzoic acid. The mixture was heated to 110-112° C. with stirring. Initially there was a vigorous gas evolution. After I hr., the mixture was poured unto ice. The mixture was made basic with conc. ammonium hydroxide (an exothermic reaction ensued). The mixture was allowed to cool to room temperature and the solid was collected by filtration. The solid was washed several time with 500 ml portions of water and then dried in vacuum and then extracted several times with warm ethyl acetate. The extracts were filtered and solvent was removed giving 57.8 g (71%) of the product.

Workup

  1. addition, the mixture was poured unto ice
  2. customan exothermic reaction
  3. temperatureto cool to room temperature
  4. filtrationthe solid was collected by filtration
  5. washThe solid was washed several time with 500 ml portions of water
  6. customdried in vacuum
  7. extractionextracted several times with warm ethyl acetate
  8. filtrationThe extracts were filtered
  9. customsolvent was removed

Sources & evidence

ORD record
ord-32694dcd0660467f832c2540f4ebf2ea
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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