Hydrochloric Acid → 3-Chloro-4-nitroaniline

HRID 1087128Notes

Reaction equation

HRID 1087128 reaction equation
Cl.C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([Cl:15])[CH:7]=1)(=O)C>O>[Cl:15][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13])[NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 236820n-(3-chloro-4-nitrophenyl)acetamide

Product 1

HCID 699963-Chloro-4-nitroanilineYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To concentrated HCl (15 mL) at reflux under nitrogen was added N-acetyl-3-chloro-4-nitroaniline (3 g, 0.014 mol). The reaction mixture was stirred for 3 hours. A white precipitate formed upon cooling to room temperature. The reaction mixture was then diluted with water, extracted with ethyl acetate and dried over sodium sulfate. The solvent was then removed under reduced pressure to afford 2.1 g (87%) of the title compound, 3-chloro-4-nitroaniline, as a yellow solid; m.p. 157°-158° C.

Workup

  1. customA white precipitate formed
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-664030bd1de947dda47dad1af3c7d97f
Source dataset
uspto-grants-1991_07
Patent number
US05034410

Reaction notes

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