Potassium Carbonate → HCID 9878216, compound

HRID 1029435Notes

Reaction equation

HRID 1029435 reaction equation
[Cl:1]C1C(C([O-])=O)=NC2C(C=1)=CC=CC=2OC.O[C:18]1[C:27]2[C:22](=[C:23]([O:28][CH3:29])[CH:24]=[CH:25][CH:26]=2)[N:21]=[C:20]([C:30]([O:32][CH3:33])=[O:31])[CH:19]=1.O=P(Cl)(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>>[Cl:1][C:18]1[C:27]2[C:22](=[C:23]([O:28][CH3:29])[CH:24]=[CH:25][CH:26]=2)[N:21]=[C:20]([C:30]([O:32][CH3:33])=[O:31])[CH:19]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 131717240HCID 131717240, compoundHCID 178498506HCID 178498506, compound

Product 1

HCID 9878216HCID 9878216, compoundYield 69%

Conditions

Temperature
80 °C

Procedure

Methyl 4™chloro-8-methoxyquinoline-2-carboxylate compound of the formula V, R5 =CH3O, R6 =H, R8 =CH3 57.6 g (247 mmol) of methyl 4-hydroxy-8-methoxyquinolinecarboxylate were introduced a little at a time into 113 ml of POCl3 at room temperature to 40° C., and the mixture was heated at 80° C. for 2 hours. The dark reaction mixture was poured onto ice and adjusted to pH 6 with concentrated K2CO3 solution. The precipitate was filtered off with suction and recrystallized from DMF/water. 42.7 g (=69%) of methyl 4-chloro-8-methoxyquinoline-2-carboxylate of melting point 139-141° C. were obtained.

Workup

  1. customThe dark reaction mixture
  2. additionwas poured onto ice
  3. filtrationThe precipitate was filtered off with suction
  4. customrecrystallized from DMF/water

Sources & evidence

ORD record
ord-674708839d7c4661a737120afec8aa25
Source dataset
uspto-grants-1992_04
Patent number
US05102892

Reaction notes

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