Nitric Acid → 4-(Benzyloxy)-5-methoxy-2-nitrobenzonitrile

HRID 896255Notes

Reaction equation

HRID 896255 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]#[N:7].[N+:19]([O-])([OH:21])=[O:20].[K]>C(O)(=O)C>[N+:19]([C:8]1[CH:9]=[C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:6]#[N:7])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7937714-Benzyloxy-3-methoxy-benzonitrileHCID 5462222Potassium

Product 1

HCID 116736184-(Benzyloxy)-5-methoxy-2-nitrobenzonitrileYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-methoxy-4-benzyloxybenzonitrile (4.78 g, 20 mmol) in acetic acid (10 ml) was slowly added to nitric acid (d=1.42, 25 ml) at 20-30° with cooling in an ice bath. The mixture was then stirred at room temperature for 6 hours. The reaction mixture was treated with potassium hydroxyde (10N) at 0° C. The basic mixture (pH 10) was extracted with CH2Cl2, the organic phase was dried over MgSO4, concentrated to give title compound (3.62 g, 64%).

Workup

  1. temperaturewith cooling in an ice bath
  2. extractionThe basic mixture (pH 10) was extracted with CH2Cl2
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cd1df245d14641e1ba3927a52ac134cd
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

Loading…