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

HRID 1466013Notes

Reaction equation

HRID 1466013 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>[Pd].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 178527696HCID 178527696, compoundCatalyst

Procedure

To a 20 mL microwave tube was added 5-bromo-2-tetralone (2.0 g, 8.9 mmol) and Palladium(0) Tetrakis (0.616 g, 0.533 mmol), zinc cyanide (1.0 g, 8.9 mmol), and DMF (8 mL). The tube was sealed, degassed and microwaved at 80° C. for 1.0 hour. TLC showed no starting material left. The mixture was diluted with ethyl acetate, washed with ammonium hydroxide (2M, 2 x), dried with sodium sulfate, filtered and evaporated under reduced pressure. The product was purified by silica gel chromatography with isocratic 30% ethyl acetate-hexane to furnish the title compound. 1H-NMR (500 MHz, CDCl3) δ ppm 7.57 (s, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.28 (d, J=7.8 Hz, 1H), 3.67 (s, 2H), 3.14 (t, J=7.0 Hz, 2H), 2.60 (t, J=7.0 Hz, 2H).

Workup

  1. customThe tube was sealed
  2. customdegassed
  3. custommicrowaved at 80° C. for 1.0 hour
  4. waitleft
  5. additionThe mixture was diluted with ethyl acetate
  6. washwashed with ammonium hydroxide (2M, 2 x)
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe product was purified by silica gel chromatography with isocratic 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-51e7c770ad784dcda345adcfb2ef3087
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…