Ethanol → 3-(1H-Indol-3-yl)prop-2-enal

HRID 920875Notes

Reaction equation

HRID 920875 reaction equation
N1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])[CH:2]=1.N#CBr.C([OH:19])C>>[NH:9]1[C:8]2[C:7](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]([CH:4]=[CH:5][CH:6]=[O:19])=[CH:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 10476Cyanogen BromideHCID 4595192-(PYRIDIN-3-YL)ANILINE

Product 1

HCID 540588453-(1H-Indol-3-yl)prop-2-enal

Procedure

To a solution of 10.0 g of 2-(pyridin-3-yl)aniline (58.7 mmol) in 100 mL ethanol is slowly added 6.2 mL of cyanogen bromide (12.4 g, 118 mmol). The reaction is heated to reflux for 1 hour, monitoring by TLC (silica, hexanes:ethyl acetate 1:1) for formation of the Zincke salt. The reaction is then quenched via addition of 50 mL saturated NH4Cl, and extracted with 3×50 mL dichloromethane. The combined organic layers are washed 3×100 mL saturated NH4Cl, followed by drying over anhydrous Na2SO4 and removal of the solvent. The crude residue is further purified via column chromatography over silica, using a hexanes-ethyl acetate gradient.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 1 hour
  3. customThe reaction is then quenched via addition of 50 mL saturated NH4Cl
  4. extractionextracted with 3×50 mL dichloromethane
  5. washThe combined organic layers are washed 3×100 mL saturated NH4Cl
  6. dry with materialby drying over anhydrous Na2SO4 and removal of the solvent
  7. customThe crude residue is further purified via column chromatography over silica

Sources & evidence

ORD record
ord-09c8d82bddaa4e97adcc57e04e9c6578
Source dataset
uspto-grants-2016_03
Patent number
US09273074B2

Reaction notes

Loading…