Nitric Acid → N-(4-formyl-2-nitrophenyl)acetamide

HRID 1188016Notes

Reaction equation

HRID 1188016 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[C:10]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)(=[O:12])[CH3:11]>>[C:10]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][C:15]=1[N+:1]([O-:4])=[O:2])(=[O:12])[CH3:11]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 739424-Acetamidobenzaldehyde

Product 1

HCID 291355N-(4-formyl-2-nitrophenyl)acetamideYield 64%

Procedure

A mixed acid was prepared by adding fuming nitric acid (1 mL), which was added 3 times as divided portions, to concentrated sulfuric acid (6 mL) under ice cooling, and added portionwise with 4-acetamidobenzaldehyde (1.91 g, 11.7 mmol). After the addition, the reaction mixture was immediately poured onto ice, and the solids were collected by filtration. The solids were sufficiently washed with cold water, dried, purified by silica gel column chromatography (developing solvent: CH2Cl2), and then recrystallized from water to obtain the target compound as pale yellow needlelike solid (1.57 g, yield: 64%).

Workup

  1. customA mixed acid was prepared
  2. additionwas added 3 times
  3. additionAfter the addition
  4. additionthe reaction mixture was immediately poured onto ice
  5. filtrationthe solids were collected by filtration
  6. washThe solids were sufficiently washed with cold water
  7. customdried
  8. custompurified by silica gel column chromatography (developing solvent: CH2Cl2)
  9. customrecrystallized from water

Sources & evidence

ORD record
ord-e85d3e0c3ad240f3970d2d9dc33d8b1f
Source dataset
uspto-grants-2014_03
Patent number
US08673957B2

Reaction notes

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