Potassium Cyanide → HCID 23292324, compound

HRID 365494Notes

Reaction equation

HRID 365494 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][C:12](=O)[CH3:13].[C-:15]#[N:16].[K+].[NH4+:18].[Cl-]>CO.O>[NH2:18][C:12]([CH3:13])([CH2:11][C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:15]#[N:16]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 25517Ammonium ChlorideHCID 10559471HCID 10559471, compound

Product 1

HCID 23292324HCID 23292324, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 6.50 g (35 mmol) of 1-(3,4-dihydronaphth-2-yl)propan-2-one in a mixture of 41 ml of CH3OH and 20 ml of water there are added, in succession, all at once, 2.34 g (36 mmol) of KCN and 1.93 g (36 mmol) of NH4Cl. After stirring for 72 hours at 20° C., the mixture is diluted with H2O and extracted with CH2Cl2 (4×50 ml). The solvents are evaporated off; the residue is taken up in Et2O and extracted again with 1N HCl (3×40 ml). The combined aqueous phases are rendered alkaline with 6N NaOH and then extracted with CH2Cl2 (3×50 ml). After drying and concentrating the organic phases, the title compound is obtained in the form of a yellow oil, which is used directly for the following reaction.

Workup

  1. additionthere are added, in succession
  2. extractionextracted with CH2Cl2 (4×50 ml)
  3. customThe solvents are evaporated off
  4. extractionextracted again with 1N HCl (3×40 ml)
  5. extractionextracted with CH2Cl2 (3×50 ml)
  6. customAfter drying
  7. concentrationconcentrating the organic phases

Sources & evidence

ORD record
ord-ee393d5df9674d75b30013dfdcb93605
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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