Sodium Iodide → 8-Iodo-3-(phenylsulfonyl)quinoline

HRID 271135Notes

Reaction equation

HRID 271135 reaction equation
N([O-])=O.[Na+].CS(O)(=O)=O.N[C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][C:17]([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[CH:16]2.C(#N)C.[I-:33].[Na+]>O.Cl.ClCCl>[I:33][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][C:17]([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[CH:16]2

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 23668193Sodium NitriteHCID 858693348-Amino-3-phenylsulfonylquinoline methanesulfonic acid salt

Product 1

HCID 114067748-Iodo-3-(phenylsulfonyl)quinoline

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of sodium nitrite (5.44 g, 78.8 mmol, 1.2 eq) in water (125 ml, 5 vol) was added to a stirred slurry of 8-amino-3-phenylsulfonylquinoline methanesulfonic acid salt (D8) (25.0 g, 65.7 mmol) in 5M HCl (500 ml, 20 vol). The mixture was stirred at 23° to 24.5° C. for 1 hr 5 min then acetonitrile (200 ml, 8 vol) was added. After 10 min a solution of sodium iodide (14.8 g, 98.6 mmol, 1.5 eq) in water (125 ml, 5 vol) was added over 3 min, resulting in the formation of a brown mixture and the evolution of gas. The brown mixture was stirred at 25° C. to 23° C. for 1 hr 5 min then dichloromethane (500 ml, 20 vol) was added and the mixture was stirred for 5 min. The lower organic layer was removed and the aqueous layer was extracted with dichloromethane (125 ml, 5 vol). The combined organic layers were washed with 10% w/v sodium sulfite (125 ml, 5 vol) then concentrated under reduced pressure. The resulting mixture was filtered and the cake was washed with acetonitrile (2×25 ml) and dried in a 40° C. oven under reduced pressure to afford the title compound D6; yield 15.27 g, 59%, identical spectroscopically to that produced by the first method.

Workup

  1. customresulting in the formation of a brown mixture
  2. stirringThe brown mixture was stirred at 25° C. to 23° C. for 1 hr 5 min
  3. stirringthe mixture was stirred for 5 min
  4. customThe lower organic layer was removed
  5. extractionthe aqueous layer was extracted with dichloromethane (125 ml, 5 vol)
  6. washThe combined organic layers were washed with 10% w/v sodium sulfite (125 ml, 5 vol)
  7. concentrationthen concentrated under reduced pressure
  8. filtrationThe resulting mixture was filtered
  9. washthe cake was washed with acetonitrile (2×25 ml)
  10. customdried in a 40° C. oven under reduced pressure

Sources & evidence

ORD record
ord-9a016404e5c14fabbaf90476cbee3439
Source dataset
uspto-grants-2008_11
Patent number
US07452888B2

Reaction notes

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