Phosphorus oxychloride → Ethyl 4-chloro-6,7,8-trifluoroquinoline-3-carboxylate

HRID 1801970Notes

Reaction equation

HRID 1801970 reaction equation
O[C:2]1[C:11]2[C:6](=[C:7]([F:14])[C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:2]1[C:11]2[C:6](=[C:7]([F:14])[C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 27339723-Quinolinecarboxylic acid, 1,4-dihydro-4-oxo-6,7,8-trifluoro-, ethyl ester

Product 1

HCID 24701792Ethyl 4-chloro-6,7,8-trifluoroquinoline-3-carboxylateYield 65.6%

Procedure

A solution of ethyl 4-hydroxy-6,7,8-trifluoroquinoline-3-carboxylate (59.0 g) and POCl3 (500 ml) was refluxed for 8 h. Excess POCl3 was distilled off, the residue was removed into the mixture of ice and water. Solid NaHCO3 was added into the mixture to pH 7˜8 and the precipitated solid was isolated by filtration. The crude was recrystallized by toluene to afford the title compound (41.3 g, 65.6% yield), mp: 110-112° C.

Workup

  1. distillationExcess POCl3 was distilled off
  2. customthe residue was removed into the mixture of ice and water
  3. additionSolid NaHCO3 was added into the mixture to pH 7˜8
  4. customthe precipitated solid was isolated by filtration
  5. customThe crude was recrystallized by toluene

Sources & evidence

ORD record
ord-258b3f5a47d74e0dbdb40870fc8f1227
Source dataset
uspto-grants-2013_01
Patent number
US08349867B2

Reaction notes

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