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

HRID 272758

Reaction equation

HRID 272758 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1)#[N:6]>C(OC(=O)C)(=O)C>[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[C:10]([N+:1]([O-:4])=[O:2])[CH:9]=1)#[N:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2897484-Acetamidophenylacetonitrile

Product 1

HCID 3490319N-(4-(Cyanomethyl)-2-nitrophenyl)acetamideYield 77%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
-10 °C

Procedure

Concentrated nitric acid (10 mL, >69% pure) was added to acetic anhydride (100 mL) cooled to −10° C. The solution was treated portionwise with N-[4-(cyanomethyl)phenyl]acetamide (5.0 g, 28.7 mmol) at a rate which maintained an internal temperature below −5° C. The solution was stirred for 1 hour while warming to room temperature. The solution was poured into an ice/water mixture and extracted several times with ethyl acetate. The combined extracts were washed with 10% Na2CO3 and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide 4.82 g (77%) of N-[4-(cyanomethyl)-2-nitrophenyl]acetamide.

Workup

  1. temperaturemaintained an internal temperature below −5° C
  2. temperaturewhile warming to room temperature
  3. extractionextracted several times with ethyl acetate
  4. washThe combined extracts were washed with 10% Na2CO3 and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-2855c4dfc13344cf90c06e6ae01e162c
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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