Nitric Acid → N-[4-(1-Cyanoethyl)-2-nitrophenyl]acetamide

HRID 660304Notes

Reaction equation

HRID 660304 reaction equation
[C:1]([CH:3]([CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)#[N:2].CC(OC(C)=O)=O.[N+:22]([O-])([OH:24])=[O:23]>O>[C:1]([CH:3]([CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([N+:22]([O-:24])=[O:23])[CH:5]=1)#[N:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 12226815N-[4-(1-Cyanoethyl)phenyl]acetamide

Product 1

HCID 12226816N-[4-(1-Cyanoethyl)-2-nitrophenyl]acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the flask of N-[4-(Cyano-methyl-methyl)-phenyl]-acetamide (12.9 g, 68.5 mmol) was added Ac2O (35 mL) at 5° C. The mixture was stirred and added HNO3 (7.45 g, 70.9 mmol) at 0° C. This reaction was very exothermic. The mixture was stirred for 1 hr at 0° C. and additionally stirred for 3 hrs at room temperature. The mixture was diluted with H2O and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:2) as eluant.

Workup

  1. stirringThe mixture was stirred for 1 hr at 0° C.
  2. stirringadditionally stirred for 3 hrs at room temperature
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-84b71eac66034e228933d48b9070f765
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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