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

HRID 1600325Notes

Reaction equation

HRID 1600325 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 and600 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 wereobtained 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, whereby 128.0 g of bicyclo[2.2.1]heptane-2,5-dicarbonitrile
  7. customwereobtained at 131°-136° C.
  8. customresults of an elemental analysis of the target product

Sources & evidence

ORD record
ord-7e6df2aef1224462a9e3d15a4f501c6b
Source dataset
uspto-grants-1998_04
Patent number
US05744504

Reaction notes

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