5-Methoxy-6-methyl-1H-indene-3-carbonitrile → 6-Methoxy-5-methyl-2,3-dihydro-1H-indene-1-carbonitrile

HRID 499009Notes

Reaction equation

HRID 499009 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH2:8][CH:7]=[C:6]2[C:13]#[N:14].[H][H]>[Pd].[Pt].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9]([CH2:8][CH2:7][CH:6]2[C:13]#[N:14])=[CH:10][C:11]=1[CH3:12]

Participants

6

Reactant 2

HCID 450913555-Methoxy-6-methyl-1H-indene-3-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 450914056-Methoxy-5-methyl-2,3-dihydro-1H-indene-1-carbonitrileYield 91.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, 0.1 gram (catalyst) of 10% palladium on carbon and 0.05 gram (catalyst) of 5% platinum on carbon were placed in a 250 mL Parr hydrogenation bottle, followed by a solution of 2.5 grams (0.014 mole) of 5-methoxy-6-methylinden-3-carbonitrile (iii) in 100 mL of ethyl acetate. The mixture was hydrogenated in a Parr hydrogenation apparatus for about 45 minutes, during which time the theoretical amount of hydrogen was taken up by the reaction. The reaction mixture was then washed through a pad of diatomaceous earth with methylene chloride. The methylene chloride wash was concentrated under reduced pressure, yielding 2.4 grams of subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. washThe reaction mixture was then washed through a pad of diatomaceous earth with methylene chloride
  2. washThe methylene chloride wash
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-5bf7589f835643a5a9236c13e124fc65
Source dataset
uspto-grants-2010_08
Patent number
US07767667B2

Reaction notes

Loading…