Phosphorus oxychloride → ethyl 6-iodo-4-chloro-3-quinolinecarboxylate

HRID 1297606Notes

Reaction equation

HRID 1297606 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=O)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([I:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:20])=O>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:20])=[CH:13][C:12]([I:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 719682Ethyl 6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Product 1

HCID 12052743ethyl 6-iodo-4-chloro-3-quinolinecarboxylateYield 98%

Procedure

A mixture of 6-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (56 g, 0.16 mol) in phosphorus oxychloride (180 mL) was refluxed under N2 for 14 h. After cooling, the solvent was removed by rotary evaporator and then by the oil pump. Sat. sodium bicarbonate (200 mL) was slowly added. The solid was collected by filtration, washed with sat. sodium bicarbonate, water and dried to obtain 4-chloro-6-iodo-quinoline-3-carboxylic acid ethyl ester (58 g, 98%) as a yellow solid.

Workup

  1. temperaturewas refluxed under N2 for 14 h
  2. temperatureAfter cooling
  3. customthe solvent was removed by rotary evaporator
  4. additionSat. sodium bicarbonate (200 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-0631c7e4fb7241668b2dd10ba3d05938
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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