Phosphorus trichloride → Dimethyl Quinoline-2,3-dicarboxylate

HRID 1955604Notes

Reaction equation

HRID 1955604 reaction equation
[N+:1]1([O-])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13][CH3:14])=[O:12])[C:2]=1[C:15]([O:17][CH3:18])=[O:16].P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13][CH3:14])=[O:12])[C:2]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 15366557HCID 15366557, compound

Product 1

HCID 11010215Dimethyl Quinoline-2,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-oxide 3 (10 mM) and phosphorus trichloride (30 mM) in anhydrous chloroform (100 ml) was refluxed for 7 h. Solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulphate and then evaporated under reduced pressure. The residue was recrystallized from isopropanol to provide the title dimethyl quinoline-2,3-dicarboxylate 7 as an off white (or light yellow) powder.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-4ee3d8d301824f80b57afcbb6894ed3d
Source dataset
uspto-grants-1998_07
Patent number
US05776935

Reaction notes

Loading…