Iodine → HCID 11845284, compound

HRID 915626Notes

Reaction equation

HRID 915626 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+].II.C(OCC)(=O)C>O>[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

6

Reactant 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 10878008HCID 10878008, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11845284HCID 11845284, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 (120 g;0.609 moles), sodium nitrite (96.6 g; 1.4 moles), iodine (31.2 g; 0.123 moles) and ethyl acetate (720 ml) were charged at room temperature and under inert gas. The mixture was heated under stirring at 40° C., then Oxistrong 15® (173.4 g) was added in 4 hours. At the end of the addition the reaction mixture was kept under stirring for 1 hour, then cooled at 20° C. Water (480 ml) was added and the mixture was kept under stirring for 1 hour. After filtration and wash of the panel with isopropyl acetate pre-cooled at 0° C. (2×120 ml) and then with water (150 ml), the solid was dried in oven under vacuum at 50° C. overnight obtaining 8-fluoro-3-nitro-2H-chromene-5-carboxylic acid amide (112.7 g; titre 91%; 70% yield).

Workup

  1. customInto a reactor, equipped with a mechanic stirrer and a reflux condenser
  2. temperatureThe mixture was heated
  3. additionOxistrong 15® (173.4 g) was added in 4 hours
  4. additionAt the end of the addition the reaction mixture
  5. stirringunder stirring for 1 hour
  6. temperaturecooled at 20° C
  7. stirringunder stirring for 1 hour
  8. filtrationAfter filtration
  9. washwash of the panel with isopropyl acetate
  10. temperaturepre-cooled at 0° C. (2×120 ml)
  11. dry with materialwith water (150 ml), the solid was dried in oven under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-b2ed860c7bb445bcba1e92a082950aaf
Source dataset
uspto-grants-2007_09
Patent number
US07265251B2

Reaction notes

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