Potassium Iodide → HCID 11845284, compound

HRID 915625Notes

Reaction equation

HRID 915625 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH:8]=[CH:7][C:6]=2[C:5]([C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1.[N:15]([O-:17])=[O:16].[Na+].[I-].[K+]>C(OCC)(=O)C>[F:1][C:2]1[C:11]2[O:10][CH2:9][C:8]([N+:15]([O-:17])=[O:16])=[CH:7][C:6]=2[C:5]([C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 10878008HCID 10878008, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11845284HCID 11845284, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

Into a reactor, equipped with a mechanic stirrer and a reflux condenser, 8-fluoro-2H-chromene-5-carboxylic acid amide (2 g; 10 mmoles), sodium nitrite (1.4 g; 20 mmoles), potassium iodide (0.33 g; 2 mmoles) and ethyl acetate (20 ml) were charged at room temperature and under inert gas. The mixture was heated at 40° C., then Oxistrong 15® (4 ml) was added in 4 hours. At the end of the addition the reaction mixture was kept under stirring for 1.5 hours, then cooled at 20° C. and diluted with ethyl acetate up to complete dissolution (about 150 ml). After washing with a 20% sodium metabisulphite solution, the phases were separated. The organic phase was washed with a saturated sodium chloride solution, dried and the solvent was removed under reduced pressure, obtaining 8-fluoro-3-nitro-2H-chromene-5-carboxylic acid amide (1.8 g; titre 88%; 66% yield).

Workup

  1. customInto a reactor, equipped with a mechanic stirrer and a reflux condenser
  2. additionOxistrong 15® (4 ml) was added in 4 hours
  3. additionAt the end of the addition the reaction mixture
  4. temperaturecooled at 20° C.
  5. washAfter washing with a 20% sodium metabisulphite solution
  6. customthe phases were separated
  7. washThe organic phase was washed with a saturated sodium chloride solution
  8. customdried
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-04a6b08253574b388d6eb9ace0c29283
Source dataset
uspto-grants-2007_09
Patent number
US07265251B2

Reaction notes

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