Toluene → 5-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 357624Notes

Reaction equation

HRID 357624 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=[O:15].C1(C)C=CC=CC=1>CN(C=O)C.O.Cl.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[C:2]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][C:10]2=[O:15])#[N:3]

Participants

8

Reactant 3

HCID 1140TolueneHCID 108895725-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 109318735-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Reagents, catalysts & solvents 4

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

0.41 g (4.5 mmol) of copper(I) cyanide is added to a solution of 1.0 g (4.4 mmol) of 5-bromo-1-tetralone [see J. Org. Chem. 49, 4226 (1984)] in 1.3 ml of DMF, and the reaction mixture is stirred at 160° for 6 hours. The reaction mixture is then cooled to 80°, and a solution of 1.6 g of iron(III) chloride hexahydrate in 2.5 ml of water and 0.44 ml of concentrated hydrochloric acid is added. Stirring is continued for 45 minutes, the reaction mixture is cooled and diluted with water, and extraction is carried out with toluene. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated by evaporation. In that manner there is obtained the title compound in the form of yellow-orange crystals, IR (CH2Cl2): 2220, 1690 cm-1 ; 1H-NMR (CDCl3): δ=8.26 (q,1H); 7.81 (q,1H); 7.43 (t,1H); 3.21 (t,2H); 2.72 (t,2H); 2.23 (m,2H).

Workup

  1. temperatureThe reaction mixture is then cooled to 80°
  2. stirringStirring
  3. waitis continued for 45 minutes
  4. temperaturethe reaction mixture is cooled
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-41aa83fbc9724966a7eb9cd293188628
Source dataset
uspto-grants-1998_11
Patent number
US05840911

Reaction notes

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