Water → 2-Oxo-1-(2-propen-1-yl)-1,2-dihydro-7-quinolinecarbonitrile

HRID 656890Notes

Reaction equation

HRID 656890 reaction equation
[I-].[C:2]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N+:11]2[CH2:14][CH:15]=[CH2:16])=[CH:6][CH:5]=1)#[N:3].[OH-:17].[K+].O>O1CCOCC1.O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[O:17]=[C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][C:4]([C:2]#[N:3])=[CH:5][CH:6]=2)[N:11]1[CH2:14][CH:15]=[CH2:16]

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68993985HCID 68993985, compound

Product 1

HCID 689923622-Oxo-1-(2-propen-1-yl)-1,2-dihydro-7-quinolinecarbonitrileYield 55%

Reagents, catalysts & solvents 2

HCID 178511488HCID 178511488, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 7-cyano-1-(2-propen-1-yl)quinolinium iodide (1.75 g, 5.4 mmol), potassium hydroxide (1.33 g, 23.76 mmol) and potassium ferricyanide (3.9 g, 11.9 mmol) in 50% 1,4-dioxane/water was stirred at rt for 2 h. Water (50 ml) was then added and the organic phase was extracted with 10% methanol/DCM (2×100 ml). The combined organic phases were washed with water (100 ml) then dried and evaporated. The residue was chromatographed on silica gel, eluting with 0-5% methanol-DCM to afford the desired compound (0.6 g, 55%).

Workup

  1. extractionthe organic phase was extracted with 10% methanol/DCM (2×100 ml)
  2. washThe combined organic phases were washed with water (100 ml)
  3. customthen dried
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 0-5% methanol-DCM

Sources & evidence

ORD record
ord-32c50c7e857a4d43916ba48d4e400688
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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