Malonic Acid → 2,4,8-Trichloro-7-methoxyquinoline

HRID 925947Notes

Reaction equation

HRID 925947 reaction equation
[ClH:1].[Cl:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[C:12](O)(=O)[CH2:13][C:14](O)=O.O(Cl)[Cl:20].[P]>O>[Cl:1][C:14]1[CH:13]=[C:12]([Cl:20])[C:6]2[C:4](=[C:3]([Cl:2])[C:9]([O:10][CH3:11])=[CH:8][CH:7]=2)[N:5]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 248201302-Chloro-3-methoxyaniline hydrochlorideHCID 178479709HCID 178479709, compound

Product 1

HCID 27945162,4,8-Trichloro-7-methoxyquinolineYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-3-methoxyaniline hydrochloride 215d (15 g, 1 eq.), malonic acid (12.06 g, 1.5 eq.), and phosphorus oxochloride (80 mL) was refluxed for 16 hrs. The reaction mixture was slowly poured into water and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified on silica pad, eluted with DCM, to yield compound 220d as a white solid in 74% yield.

Workup

  1. temperaturewas refluxed for 16 hrs
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified on silica pad
  7. washeluted with DCM

Sources & evidence

ORD record
ord-964eb2fc958e476b84c7e6dd05937534
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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