Potassium Cyanide → HCID 22107240, compound

HRID 726767Notes

Reaction equation

HRID 726767 reaction equation
[OH:1][C:2]1[C:15]2[C:6](=[O+:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[C:4]([OH:16])[CH:3]=1.[C-:17]#[N:18].[K+]>CN(C)C=O>[C:17]([CH:14]1[C:15]2[C:2]([OH:1])=[CH:3][C:4]([OH:16])=[CH:5][C:6]=2[O:7][C:8]2[C:13]1=[CH:12][CH:11]=[CH:10][CH:9]=2)#[N:18]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 19707529HCID 19707529, compound

Product 1

HCID 22107240HCID 22107240, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15.5 g (50.0 mmol) of 1,3-dihydroxy-xanthenium bisulfam [R. K. M. Pillai et al, J. Org. Chem. 51, 717 (1986)] and 4.90 g (75.0 mmol) of potassium cyanide in 150 ml of dimethylformamide is kept at 130° C. for 2 hours. The solvent is then concentrated on a vacuum rotary evaporator and the residue is taken up in ethyl acetate. The ethyl acetate phase is washed with water, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Chromatography of the residue over silica gel using the mobile phase system hexane/ethyl acetate=3:1 and crystallization of the pure fractions from ethyl acetate gives 10.0 g (83%) of 9-cyano-1,3-dihydroxy-xanthene, melting point 211°-215° C. (compound (107), Table 1).

Workup

  1. concentrationThe solvent is then concentrated on a vacuum rotary evaporator
  2. washThe ethyl acetate phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated on a vacuum rotary evaporator
  5. customChromatography of the residue over silica gel using the mobile phase system hexane/ethyl acetate=3:1 and crystallization of the pure fractions from ethyl acetate

Sources & evidence

ORD record
ord-a8fb5d432a514bbd9d239da58858a39f
Source dataset
uspto-grants-1998_01
Patent number
US05710198

Reaction notes

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