Nitrobenzene → 6-Iodoquinolin-3-ol

HRID 219193Notes

Reaction equation

HRID 219193 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1C(O)=O)=[CH:9][C:8]([I:15])=[CH:7][CH:6]=2.[N+](C1C=CC=CC=1)([O-])=O.CCN(C(C)C)C(C)C>>[I:15][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[CH:3][C:2]([OH:1])=[CH:11]2

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 81531DiisopropylethylamineHCID 598430503-Hydroxy-6-iodoquinoline-4-carboxylic acid

Product 1

HCID 598430856-Iodoquinolin-3-ol

Conditions

Temperature
210 °C

Procedure

3-hydroxy-6-iodoquinoline-4-carboxylic acid (22 g, 70 mmol) was suspended in 1-nitrobenzene (143 ml, 1397 mmol) followed by adding Hunig's base (25 mL)—the suspension was completely dissolved. The resulting mixture was heated to reflux (210° C.) under N2. After 3 h, LC/MS showed no sign of starting material mass. The reaction mixture was cooled to rt; solvent was removed as much as possible in vacuo. The crude product was redissolved in DCM/MeOH and the solid was collected by filtration. The solid was rinsed with hexane and either and dried as brownish solid. The filtrate was removed excess solvent and purified using SiO2 chromatography (TELEDYNE ISCO REDISEP®, P/N 68-2203-058, 330 g SiO2, solvent system: hexanes:acetone=80%:20%, Flow=100 mL/min) to afford the desired product as brown solid. MS m/z: 272.3 (M+H). Calc'd. for C9H6INO−271.05.

Workup

  1. dissolutionwas completely dissolved
  2. temperatureThe resulting mixture was heated
  3. temperatureThe reaction mixture was cooled to rt
  4. customsolvent was removed as much as possible in vacuo
  5. dissolutionThe crude product was redissolved in DCM/MeOH
  6. filtrationthe solid was collected by filtration
  7. washThe solid was rinsed with hexane
  8. customeither and dried as brownish solid
  9. customThe filtrate was removed excess solvent
  10. custompurified

Sources & evidence

ORD record
ord-03af85f625964f46a615bdad71dfdb57
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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