Phosphorus oxychloride → HCID 10385151, compound

HRID 1588738Notes

Reaction equation

HRID 1588738 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24].P(Cl)(Cl)([Cl:27])=O>N1C=CC=CC=1>[Cl:27][C:7]1[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 11726135HCID 11726135, compound

Product 1

HCID 10385151HCID 10385151, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of ethyl 6-chloro-4-(2-chlorophenyl)-1,2-dihydro -2-oxo-3-quinolinecarboxylate (1.0 g), phosphorus oxychloride (5 ml) and pyridine (0.5 ml) was refluxed for 16 hours. The mixture was concentrated under reduced pressure. Water was added to the residue to obtain ethyl 2,6-dichloro-4-(2-chlorophenyl)-3-quinolinecarboxylate (0.7 g). The product was dissolved in methanol (20 ml), to which 28% sodium methoxide-methanol solution (0.5 ml) was added. The mixture was refluxed for 3 hours, and then diluted with water to obtain methyl 6-chloro-4-(2-chlorophenyl) -2-methoxy-3-quinolinecarboxylate as crystals (0.61 g, 61.0%). Recrystallization from methanol gave colorless needles. mp 151°-152° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionWater was added to the residue

Sources & evidence

ORD record
ord-43c696b5bbb44259bd52b3696153d710
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

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