Chlorosuccinimide → HCID 178486799, compound

HRID 394987

Reaction equation

HRID 394987 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][CH:15]=[C:14]2[OH:23]>C(O)(=O)C>[Cl:1][C:15]1[CH:16]=[N:17][C:18]2[C:13]([C:14]=1[OH:23])=[CH:12][C:11]([O:10][CH3:9])=[C:20]([O:21][CH3:22])[CH:19]=2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178486804HCID 178486804, compound

Product 1

HCID 178486799HCID 178486799, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

5.45 g of N-chlorosuccinimide were added to a solution of 6,7-dimethoxyquinolin-4-ol in 300 cm3 of acetic acid, with stirring and at a temperature in the region of 20° C. The reaction mixture was heated at a temperature in the region of 50° C. for 6 hours. After cooling to about 20° C. and stirring for 18 hours at this same temperature, the reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. One hundred cm3 of sodium hydrogen carbonate solution were added dropwise to the evaporation residue and the suspension was then stirred for 24 hours in the region of 20° C. The insoluble material was filtered off and then dried in an oven under reduced pressure (20 Pa). 5.39 g of 3-chloro-4-hydroxy-6,7-dimethoxyquinoline were obtained in the form of a dark green solid.

Workup

  1. temperatureThe reaction mixture was heated at a temperature in the region of 50° C. for 6 hours
  2. temperatureAfter cooling to about 20° C.
  3. stirringstirring for 18 hours at this same temperature
  4. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  5. additionOne hundred cm3 of sodium hydrogen carbonate solution were added dropwise to the evaporation residue
  6. stirringthe suspension was then stirred for 24 hours in the region of 20° C
  7. filtrationThe insoluble material was filtered off
  8. customdried in an oven under reduced pressure (20 Pa)

Sources & evidence

ORD record
ord-881b90c90cdb4d1a85363a3bb0297564
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Linked notes

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