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

HRID 2173250Notes

Reaction equation

HRID 2173250 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[CH2:15][CH2:14][CH2:13][C:12](=[O:17])[C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[CH3:20][N:21](C=O)C>C(Cl)Cl.[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:17]=[C:12]1[CH2:13][CH2:14][CH2:15][C:16]2[C:7]([C:20]#[N:21])=[CH:8][CH:9]=[CH:10][C:11]1=2

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 11748402HCID 11748402, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of compound 5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate (8.6 g, 30.8 mmol), Zn(CN)2(7.2 g, 61.6 mmol) and Pd(PPh3)4(0.8 g) in anhydrous DMF was stirred at 120° C. under N2 overnight. The reaction was cooled to ambient temperature, and then diluted with DCM. Filtered off solids and the orgainic filtrate was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified with silica gel cloumn chromatography to give 5-oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. filtrationFiltered off solids
  3. washthe orgainic filtrate was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel cloumn chromatography

Sources & evidence

ORD record
ord-3c51cdd5f02b483c80b9c870d46746a7
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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