Hydrochloric Acid → 4-Amino-3-nitrobenzaldehyde

HRID 1188017

Reaction equation

HRID 1188017 reaction equation
C([NH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14])(=O)C.Cl>CO>[NH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 291355N-(4-formyl-2-nitrophenyl)acetamide

Product 1

HCID 132377034-Amino-3-nitrobenzaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Acetamido-3-nitrobenzaldehyde (2.08 g, 10 mmol) was dissolved in methanol (200 mL). The solution was added with aqueous 2 N HCl (50 mL), and refluxed by heating at 80° C. for 8 hours under an argon flow. The reaction mixture was concentrated under reduced pressure to remove the methanol, and the residue was made basic with aqueous 2 N NaOH, and extracted 5 times with dichloromethane. The organic phases were combined, dried over anhydrous Na2SO4, and concentrated under reduced pressure to obtain the target compound as yellow solid (1.62 g, yield: 98%).

Workup

  1. temperaturerefluxed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto remove the methanol
  4. extractionextracted 5 times with dichloromethane
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a3789caf9ded4a6d987a5ba0fdfd8cfa
Source dataset
uspto-grants-2014_03
Patent number
US08673957B2

Linked notes

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