Benzene → Bicyclo[2.2.1]heptane-2,5-dicarbonitrile

HRID 362171Notes

Reaction equation

HRID 362171 reaction equation
F[C:2](F)(F)[C:3]([NH:5]OC(=O)C(F)(F)F)=O.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH:21]1C=CC=C[CH:22]=1>O>[CH:17]12[CH2:16][CH:22]([CH:19]([C:20]#[N:15])[CH2:18]1)[CH2:21][CH:2]2[C:3]#[N:5]

Participants

5

Reactant 3

HCID 241BenzeneHCID 1049PyridineHCID 69634(2,2,2-Trifluoroacetyl)azanyl 2,2,2-trifluoroacetate

Product 1

HCID 15745024Bicyclo[2.2.1]heptane-2,5-dicarbonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a 2- flask equipped with a stirrer, a thermometer and a reflux condenser, 179.0 g (1.2 moles) of 5-cyano-bicyclo[2.2.1]hepta-2-carbaldehyde, 292.6 g (1.3 moles) of N,O-bis(trifluoroacetyl)hydroxylamine, 197.8 g (2.5 moles) of pyridine and 600 m of benzene were charged. The resulting mixture was gradually heated and refluxed for 3 hours under stirring. Deionized water (500 m) was thereafter added to the reaction mixture. The water layer so obtained was removed, whereby an oil was obtained. The oil was distilled under reduced pressure, whereby 128.0 g of bicyclo[2.2.1]heptane-2,5-dicarbonitrile were obtained at 131°-136° C./1 mmHg (yield: 73%). The following is the results of an elemental analysis of the target product.

Workup

  1. customIn a 2- flask equipped with a stirrer
  2. temperatureThe resulting mixture was gradually heated
  3. temperaturerefluxed for 3 hours
  4. customwas removed
  5. customwhereby an oil was obtained
  6. distillationThe oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-a755affe91ba4f8199e3fa4c0acb43cb
Source dataset
uspto-grants-1999_02
Patent number
US05869184

Reaction notes

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