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

HRID 2220165Notes

Reaction equation

HRID 2220165 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-61f3ffebb77f4409b67f9643101f0447
Source dataset
uspto-grants-2008_08
Patent number
US07417057B2

Reaction notes

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