Hydrochloric Acid → 5-(3-Aminophenyl)pent-4-yn-1-ol

HRID 1944876Notes

Reaction equation

HRID 1944876 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]#[C:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]#[C:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 575169425-(3-Nitrophenyl)pent-4-yn-1-ol

Product 1

HCID 575169435-(3-Aminophenyl)pent-4-yn-1-ol

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A solution of Intermediate 46 (16 mmol) in ethanol (80 mL) was treated successively with 10% aqueous hydrochloric acid solution (4 mL) and iron powder and then was lowered in to a 95° C. oil bath. After 90 minutes of reflux heating, the mixture was deemed complete by LC/MS analysis and was filtered while hot through a pad of Celite diatomaceous earth, eluting with methanol. The filtrate was concentrated to dryness under reduced pressure. The residue was purified via automated flash silica gel chromatography, using a 40 g Silicycle SiliSep flash column (hexanes/ethyl acetate). Concentration of the desired fractions under reduced pressure provided the title compound. ES/MS calcd. for C11H14NO+ 176.1. Found m/z=176.2 (M+H)+.

Workup

  1. customwas lowered in to a 95° C. oil bath
  2. temperatureAfter 90 minutes of reflux
  3. temperatureheating
  4. filtrationwas filtered while hot through a pad of Celite diatomaceous earth
  5. washeluting with methanol
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure
  7. customThe residue was purified via automated flash silica gel chromatography

Sources & evidence

ORD record
ord-b0c73cb86fd84460b599244ecff832eb
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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