Water → 3-Methoxy-4-nitrobenzonitrile

HRID 417216Notes

Reaction equation

HRID 417216 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([NH2:8])=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]#[N:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 110633383-Methoxy-4-nitrobenzamide

Product 1

HCID 108992273-Methoxy-4-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-methoxy-4-nitrobenzamide (8 g, 41 mmol) in dioxane (300 mL) was added pyridine (32 g, 408 mmol), followed by dropwise addition of trifluoroacetic anhydride (43 g, 204 mmol). The reaction mixture was stirred at room temperature for 5 h. Water was added to quench the reaction. The mixture was concentrated, then the residue was partitioned between ethyl acetate and water. The organic layer was separated, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, aqueous saturated CuSO4 solution, brine, dried over MgSO4, and concentrated to give 3-methoxy-4-nitrobenzonitrile as a off white solid (6.5 g, 90%)

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationThe mixture was concentrated
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washwashed with water, aqueous saturated CuSO4 solution, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-87b44dfab667429985be50a3063acf76
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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