Dimethylformamide → 6-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1519481Notes

Reaction equation

HRID 1519481 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[CH2:7]2.[CH3:13][N:14](C=O)C>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.[C-]#N.[Zn+2].[C-]#N>[O:12]=[C:6]1[CH2:5][CH2:4][C:3]2[CH:2]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:8]=2[CH2:7]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 40596895-Bromo-2-tetralone

Product 1

HCID 162445046-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

The 5-bromo-2 tetralone (2.0 g, 8.9 mmol), tetrakis(triphenylphosphine)palladium (0.62 g, 0.53 mmol) and zinc cyanide (0.73 g, 6.2 mmol) were added to 4 ml DMF in a 20 ml microwave tube. The mixture was degassed and microwaved at 80° C. for 30 mins. TLC showed no starting material left and the mixture was diluted with ethyl acetate and washed with ammonium hydroxide (2M, ×4 ml). The organic layer was separated and dried over Na2SO4 then filtered. The solvent was evaporated under reduced pressure. The residue was chromatographed through 40 gm Isco Redi-sep column and eluted with 0-30% ethyl acetate-hexane to yield 6-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile.

Workup

  1. customThe mixture was degassed
  2. custommicrowaved at 80° C. for 30 mins
  3. waitleft
  4. additionthe mixture was diluted with ethyl acetate
  5. washwashed with ammonium hydroxide (2M, ×4 ml)
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationthen filtered
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was chromatographed through 40 gm Isco Redi-sep column
  11. washeluted with 0-30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-695c76498fa64d55931d4f8907676657
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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