4-Hydroxy-3-nitro-5-[(1E)-prop-1-en-1-yl]benzonitrile → 3-Amino-4-hydroxy-5-propylbenzonitrile

HRID 2093628Notes

Reaction equation

HRID 2093628 reaction equation
[OH:1][C:2]1[C:9](/[CH:10]=[CH:11]/[CH3:12])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:13]([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:13][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH2:10][CH2:11][CH3:12])[C:2]=1[OH:1])[C:6]#[N:7]

Participants

4

Reactant 1

HCID 687853344-Hydroxy-3-nitro-5-[(1E)-prop-1-en-1-yl]benzonitrile

Product 1

HCID 687414503-Amino-4-hydroxy-5-propylbenzonitrileYield 26%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.78 g of 4-hydroxy-3-nitro-5-[(1E)-prop-1-en-1-yl]benzonitrile in ethyl acetate (10 ml) was added palladium on carbon (100 mg). This mixture was evacuated and flushed with hydrogen (via balloon) 10 times. The reaction was stirred at room temperature for 14 h under hydrogen. The mixture was then filtered through a plug of Celite, eluting with methanol. After concentration of the eluent in vacuo, the residue was further purified by column chromatography on a Biotage Horizon, eluting with 1 column volume of 100% hexanes followed by a gradient of 0-20% ethyl acetate in hexanes over 10 column volumes to provide the title compound (400 mg, 26%). Mass spectrum (ESI) 177.2 (M+1).

Workup

  1. customThis mixture was evacuated
  2. customflushed with hydrogen (via balloon) 10 times
  3. filtrationThe mixture was then filtered through a plug of Celite
  4. washeluting with methanol
  5. customAfter concentration of the eluent in vacuo, the residue was further purified by column chromatography on a Biotage Horizon
  6. washeluting with 1 column volume of 100% hexanes

Sources & evidence

ORD record
ord-71ac7e3b36c5490995e3a321899867ed
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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