Potassium Cyanide → HCID 59233918, compound

HRID 1661066Notes

Reaction equation

HRID 1661066 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7]/[C:8]/2=[C:11](/[C:17]#[N:18])\C(OCC)=O)=[CH:4][CH:3]=1.[C-:19]#[N:20].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH2:11][C:17]#[N:18])[C:19]#[N:20])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 68217609HCID 68217609, compound

Product 1

HCID 59233918HCID 59233918, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of (E)-ethyl 2-cyano-2-(6-chloro-2,3-dihydro-1H-inden-1-ylidene)acetate (Prep38, 15.00 g, 0.06 mol) in ethanol (300 ml) was treated with a solution of KCN (9.75 g, 0.15 mol) in water (90 ml). The mixture was warmed to 65° C., and stirred for 16 h. The mixture was concentrated in vacuo to remove solvent. The residue was extracted with EA (100 ml×3). The organic layers were combined and washed with a saturated solution of NaHCO3, brine and dried over Na2SO4. The crude was purified by FC (P:E=10/1) to obtain the title compound (4.60 g, y=37.1%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove solvent
  3. extractionThe residue was extracted with EA (100 ml×3)
  4. washwashed with a saturated solution of NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. customThe crude was purified by FC (P:E=10/1)

Sources & evidence

ORD record
ord-907e7eae66824b7e89291ff3fb18e0dd
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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