Potassium Cyanide → 3-Butyl-6-cyano-phthalide

HRID 2120186Notes

Reaction equation

HRID 2120186 reaction equation
N[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:12][CH2:13][CH2:14][CH3:15])[O:7][C:8]2=[O:9])=[CH:4][CH:3]=1.N([O-])=O.[Na+].[C-:20]#[N:21].[K+]>Cl.O>[CH2:12]([CH:6]1[C:5]2[C:10](=[CH:11][C:2]([C:20]#[N:21])=[CH:3][CH:4]=2)[C:8](=[O:9])[O:7]1)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 98777066-Amino-3-butyl-phthalideHCID 23668193Sodium Nitrite

Product 1

HCID 234391233-Butyl-6-cyano-phthalide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A suspension of 7.2 g (32.12 mmol) of the compound obtained in Example 4 in 100 ml of 18% hydrochloric acid is diazotized by a solution of 6 g of sodium nitrite in 30 ml of water at 3-5° C. To this solution there is added, with vigorous stirring, a solution of cuprous cyanide, prepared from 21.0 g of CuSO4.5H2O in 87 ml of H2O and 24.7 g of potassium cyanide in 133 ml of H2O at 50-60° C. The mixture is stirred at the same temperature for 2 hours. The separated solid is extracted with methylene chloride, the organic phase is washed with sodium carbonate solution and water. After removing the solvent, the residue is crystallised from ethanol to give the title compound.

Workup

  1. additionTo this solution there is added, with vigorous stirring
  2. extractionThe separated solid is extracted with methylene chloride
  3. washthe organic phase is washed with sodium carbonate solution and water
  4. customAfter removing the solvent
  5. customthe residue is crystallised from ethanol

Sources & evidence

ORD record
ord-f69a39297361486f93e853a2da2eca61
Source dataset
uspto-grants-2004_02
Patent number
US06689808B2

Reaction notes

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