Iodine → 6-Iodoquinolin-2(1H)-one

HRID 986009Notes

Reaction equation

HRID 986009 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=[O:11].[I:12]I.C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Ag+2]>[I:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][C:2](=[O:11])[CH:3]=[CH:4]2

Participants

6

Reactant 3

HCID 807IodineHCID 60382-HydroxyquinolineHCID 10340Sodium Carbonate

Product 1

HCID 138361846-Iodoquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-[1H]-quinolone (2.0 g) and silver sulphate (2.14 g) in concentrated sulphuric acid (15.0 cm3) was stirred at room temperature during the addition of iodine (3.5 g). After heating at 50° for 24 hours the mixture was poured onto ice, the solution was neutralised with solid sodium carbonate and the solid was filtered off. This material was chromatographed on silica (Merck "MK 60.9385") eluting with chloroform to affford a residue which was recrystallised from methanol to give 6-iodo-2-[1H]-quinolone, m.p. 261°, (0.8 g).

Workup

  1. temperatureAfter heating at 50° for 24 hours the mixture
  2. additionwas poured onto ice
  3. filtrationthe solid was filtered off
  4. customThis material was chromatographed on silica (Merck "MK 60.9385")
  5. washeluting with chloroform
  6. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-fbb58fe211224c9fbe3e2df1b30333dd
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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