4-Hydroxy-3-isopropenyl-5-nitrobenzonitrile → HCID 57917216, compound

HRID 2093615Notes

Reaction equation

HRID 2093615 reaction equation
[OH:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:13]([CH3:15])=[CH2:14]>C(OCC)(=O)C.[Pd]>[NH2:10][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([CH:13]([CH3:15])[CH3:14])[C:2]=1[OH:1])[C:6]#[N:7]

Participants

4

Reactant 1

HCID 671407854-Hydroxy-3-isopropenyl-5-nitrobenzonitrile

Product 1

HCID 57917216HCID 57917216, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-3-isopropenyl-5-nitrobenzonitrile (4.135 g, 20.25 mmol) in ethyl acetate (100 ml) was added 1.2 g of Pd/C. The resulting mixture was degassed and flushed with nitrogen, and then degassed and flushed with hydrogen using a double balloon. The reaction was stirred under hydrogen for 14 h, and then diluted with ethyl acetate, filtered through a pad of Celite and concentrated. The residue was purified by flash column chromatography using a Horizon Biotage, 65i Si column, eluting with 1 column volume of dichloromethane, followed by a linear gradient of ethyl acetate in dichloromethane from 0% to 50% over 10 column volume. It was then repurified by flash column chromatography using a Horizon Biotage, 65i Si column, eluting with 1 column volume of 5% ethyl acetate in hexanes, followed by a linear gradient of ethyl acetate in hexanes from 5% to 100% over 10 column volumes to afford the title compound. Mass spectrum (ESI) 177.4 (M+1).

Workup

  1. customThe resulting mixture was degassed
  2. customflushed with nitrogen
  3. customdegassed
  4. customflushed with hydrogen using a double balloon
  5. additiondiluted with ethyl acetate
  6. filtrationfiltered through a pad of Celite
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography
  9. washeluting with 1 column volume of dichloromethane
  10. customIt was then repurified by flash column chromatography
  11. washeluting with 1 column volume of 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ac7ba380441b49a7be46199332221d5b
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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