Potassium Iodide → HCID 67603160, compound

HRID 362670Notes

Reaction equation

HRID 362670 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][C:9]2[CH2:12][C:11](=[O:13])[C:10]=2[CH:14]=1.[I-:15].[K+]>O.S(=O)(=O)(O)O>[I:15][C:6]1[CH:7]=[CH:8][C:9]2[CH2:12][C:11](=[O:13])[C:10]=2[CH:14]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 12067468Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 4-amino-HCID 23668193Sodium Nitrite

Product 1

HCID 67603160HCID 67603160, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 1118Sulfuric AcidSolvent

Procedure

At 0°-5° C., a solution of sodium nitrite (0.759 g) in water (5 mL) was added into a suspension of the amine 8 in 2.5 mL of concentrated sulfuric acid and 10 mL of water. After stirring for 15 minutes, a solution of potassium iodide (1.826 g) in 3 mL of water was added slowly. The cloudy, orange-purple solution was stirred at room temperature for 1 hour. The reaction mixture was diluted with water (50 mL) and extracted with with ether (2×100 mL). The etheral extracts were washed with aqueous sodium carbonate solution and water. Removal of solvent and flash chromatography of the residue afforded the iodide 17. 1H NMR (200 MHz, CDCl3) 4.00 (s, 2H), 7.27 (d d, 1H), 7.48 (d d, 1H), 8.13 (s, 1H); MS (EI, m/e, relative intensity %) 244 (M+., 12), 216 (M+. -CO, 7.8), 89 (216 (M+. -CO -.I, 40).

Workup

  1. stirringThe cloudy, orange-purple solution was stirred at room temperature for 1 hour
  2. extractionextracted with with ether (2×100 mL)
  3. washThe etheral extracts were washed with aqueous sodium carbonate solution and water
  4. customRemoval of solvent and flash chromatography of the residue

Sources & evidence

ORD record
ord-b658085a3e834812a988cfa88276b2c5
Source dataset
uspto-grants-1999_02
Patent number
US05869693

Reaction notes

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