Dimethylformamide → Methyl 4-chloroquinoline-7-carboxylate

HRID 964999Notes

Reaction equation

HRID 964999 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([Cl:14])=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[OH-].[K+].[CH3:17]N(C)C=O.CI>CO>[CH3:17][O:2][C:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([Cl:14])=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 217084474-Chloroquinoline-7-carboxylic acid

Product 1

HCID 21708520Methyl 4-chloroquinoline-7-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Carboxy-4-chloroquinoline (5 g, 24.0 mmol) was dissolved in a mixed solution of potassium hydroxide (1.49 g, 26.6 mmol) with methanol (150 ml) and stirred at room temperature overnight. The reactant was evaporated to dryness under reduced pressure. The residue was added with dimethylformamide (DMF; 60 ml) and methyl iodide (3.5 g, 24.6 mmol) in the order named and stirred at 80° C. for an hour. The reaction mixture was poured into ice water. The resulting precipitates were collected by filtration, dried over phosphorus pentoxide and recrystallized from ethanol (20 ml) to obtain 3.6 g (61%) of 7-methoxycarbonyl-4-chloroquinoline.

Workup

  1. customThe reactant was evaporated to dryness under reduced pressure
  2. stirringstirred at 80° C. for an hour
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. dry with materialdried over phosphorus pentoxide
  6. customrecrystallized from ethanol (20 ml)

Sources & evidence

ORD record
ord-20bf0396583544dd8eeed57160461e66
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

Loading…