Thionyl Chloride → Ethyl 7-(3,5-dimethyl-4-isoxazolyl)-4-chloro-3-quinolinecarboxylate

HRID 1042991Notes

Reaction equation

HRID 1042991 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11](O)=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[N:14]3)=[CH:9][CH:8]=2)=[C:5]([CH3:23])[O:4][N:3]=1.S(Cl)([Cl:26])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([Cl:26])=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[N:14]3)=[CH:9][CH:8]=2)=[C:5]([CH3:23])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 178469490HCID 178469490, compound2×

Product 1

HCID 57465582Ethyl 7-(3,5-dimethyl-4-isoxazolyl)-4-chloro-3-quinolinecarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 7-(3,5-dimethyl-4-isoxazolyl)-4-hydroxy-3-quinolinecarboxylate (for a preparation see Intermediate 7, 20 g, 64.04 mmol) was reacted with thionyl chloride (326 ml) and heated to reflux overnight. Excess thionyl chloride was co-evaporated with toluene. The crude product was triturated with iPr2O and filtered to give the title compound as a brown powder (20.15 g, 95%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe crude product was triturated with iPr2O
  4. filtrationfiltered

Sources & evidence

ORD record
ord-39bef6f1ee1743ab92d3f960edd8c7b7
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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