Phosphorus oxychloride → 2-Chloro-6-iodo-quinoline

HRID 1295446Notes

Reaction equation

HRID 1295446 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH:6]=[CH:5]2.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 138361846-Iodoquinolin-2(1H)-one

Product 1

HCID 198986972-Chloro-6-iodo-quinolineYield 87%

Procedure

A mixture of 6-iodo-1H-quinolin-2-one (6.23 g, 23 mmol) in phosphorus oxychloride (25 mL) was refluxed under N2 for 2 h. After cooling, the solvent was removed by rotary evaporator and then by the oil pump. Sat. sodium bicarbonate (100 mL) was slowly added. The solid was collected by filtration, washed with sat. sodium bicarbonate, water and dried to obtain 2-chloro-6-iodo-quinoline (5.78 g, 87%) as a black solid. LC-MS m/e 290 (MH+).

Workup

  1. temperaturewas refluxed under N2 for 2 h
  2. temperatureAfter cooling
  3. customthe solvent was removed by rotary evaporator
  4. additionSat. sodium bicarbonate (100 mL) was slowly added
  5. filtrationThe solid was collected by filtration
  6. washwashed with sat. sodium bicarbonate, water
  7. customdried

Sources & evidence

ORD record
ord-e89e09efcfa1429c93d00410f6e67515
Source dataset
uspto-grants-2007_07
Patent number
US07241893B2

Reaction notes

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