Phosphorus oxychloride → 4-Chloro-6-iodoquinoline-3-carbonitrile

HRID 1297629Notes

Reaction equation

HRID 1297629 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]([C:12]#[N:13])[C:5]2=O.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:8]=[CH:7][C:6]=1[C:12]#[N:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 289765906-Iodo-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Product 1

HCID 224667694-Chloro-6-iodoquinoline-3-carbonitrileYield 98%

Procedure

A mixture of 6 6-iodo-4-oxo-1,4-dihydro-quinoline-3-carbonitrile (example 14b) (100 g, 0.34 mol) in phosphorus oxychloride (300 mL) was refluxed under N2 for 7 h. After cooling, the solvent was removed by rotary evaporator and then by the oil pump. Sat. sodium bicarbonate (200 mL) and ice water were slowly added. The solid was collected by filtration, washed with sat. sodium bicarbonate, water and dried to obtain 4-chloro-6-iodo-quinoline-3-carbonitrile (58 g, 98%) as a yellow solid. LC-MS m/e 315 (MH+).

Workup

  1. temperaturewas refluxed under N2 for 7 h
  2. temperatureAfter cooling
  3. customthe solvent was removed by rotary evaporator
  4. additionSat. sodium bicarbonate (200 mL) and ice water were slowly added
  5. filtrationThe solid was collected by filtration
  6. washwashed with sat. sodium bicarbonate, water
  7. customdried

Sources & evidence

ORD record
ord-2fda928f72ed4c278ade8f07219a366f
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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