Dimethyl Sulfoxide → HCID 1486468, compound

HRID 1656436Notes

Reaction equation

HRID 1656436 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][CH:17]=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])C(OCC)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].CS(C)=O>O>[Cl:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][CH:12]=1)[N:16]=[CH:17][C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:1]2[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 433294Lithium ChlorideHCID 3813534HCID 3813534, compound

Product 1

HCID 1486468HCID 1486468, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of diethyl (2-benzoyl-4-chlorophenyl)aminomethylenemalonate (7.0 g), lithium chloride (3.7 g) and dimethyl sulfoxide (70 ml) was heated for 1.5 hrs. at 180° C. The mixture was diluted with water to give ethyl 6-chloro-4-phenyl-3-quinolinecarboxylate as crystals (3.8 g, 70.0%), which was recrystallized from ethanol as needles. m.p. 123°-124° C.

Workup

  1. temperaturewas heated for 1.5 hrs
  2. customat 180° C

Sources & evidence

ORD record
ord-458175b4cdf7477f9014cd2a956c8d7e
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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