Potassium Cyanide → 5-chloro-1-(cyanomethyl)-6-methoxy-2,3-dihydro-1H-indene-1-carbonitrile

HRID 1661056Notes

Reaction equation

HRID 1661056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])/[C:7](=[C:13](\[C:19]#[N:20])/C(OCC)=O)/[CH2:6][CH2:5]2.[C-:21]#[N:22].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7]([CH2:13][C:19]#[N:20])([C:21]#[N:22])[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 68217647HCID 68217647, compound

Product 1

HCID 674292935-chloro-1-(cyanomethyl)-6-methoxy-2,3-dihydro-1H-indene-1-carbonitrileYield 16%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
67.5 °C

Procedure

To a solution of (E)-ethyl 2-(5-chloro-6-methoxy-2,3-dihydro-1H-inden-1-ylidene)-2-cyanoacetate (Prep16, 6.02 g, 24.4 mmol) in ethanol (25 ml) was added a solution of KCN (3.61 g, 60 mmol) in water. The mixture was stirred for one day at 65-70° C. Water was added and extracted with ethyl acetate twice. The organic phases were combined and dried over anhydrous Na2SO4, concentrated and purified by FC to afford the title compound (800 mg, y=16%).

Workup

  1. extractionextracted with ethyl acetate twice
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. custompurified by FC

Sources & evidence

ORD record
ord-3a67432d36d3459796066ccb5ea4e697
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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