Potassium Iodide → HCID 19895603, compound

HRID 1073933Notes

Reaction equation

HRID 1073933 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]3[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=3[O:11][C:10]([CH3:21])([CH3:20])[CH:9]=2)=[N:6][CH:7]=1.N([O-])=O.[Na+].[I-:26].[K+].[OH-].[Na+]>C(O)(=O)C.O>[I:26][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]3[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=3[O:11][C:10]([CH3:21])([CH3:20])[CH:9]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 19895584HCID 19895584, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19895603HCID 19895603, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

9.5 g of 4-(5-amino-2-pyridyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile were dissolved in 150 ml of acetic acid and 100 ml of water. 3.16 g of sodium nitrite in 10 ml of water were added at such a rate as to keep the temperature below 5° C. After 15 minutes 23 g of potassium iodide in 20 ml of water were added and the mixture was stirred at room temperature for 1 hour. The mixture was then poured into 1 l of 2M sodium hydroxide solution and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution to give 4.78 g of 4-(5-iodo-2-pyridyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile which was used without further purification.

Workup

  1. customthe temperature below 5° C
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-3fd60ee5ef4549f58bf87bb8d4fe19f0
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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