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

HRID 264601Notes

Reaction equation

HRID 264601 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-l 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 ml of benzene were charged. The resulting mixture was gradually heated and refluxed for 3 hours under stirring. Deionized water (500 ml) 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-l 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-3da37bdd4ac54b18bb6a3ee80a58eb69
Source dataset
uspto-grants-1997_07
Patent number
US05646240

Reaction notes

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