Malonic Acid → 2-Chloro-4,6-dimethoxyquinoline

HRID 1666661Notes

Reaction equation

HRID 1666661 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH3:15][O:16]C1C=CC(N)=CC=1.C(O)(=O)CC(O)=O.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]([O:16][CH3:15])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 7732P-AnisidineHCID 9483562,4-Dichloro-6-methoxyquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 579701022-Chloro-4,6-dimethoxyquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,4-dichloro-6-methoxyquinoline (0.97 g) synthesized from p-anisidine and malonic acid according to the method of WO200226713 in methanol (20 mL) was added sodium methoxide (1.37 g), and the mixture was stirred at 70° C. for 3 h. The reaction solution was added dropwise to ice water, and the resulting solids were collected by filtration. The resulting solids were purified by silica gel column chromatography (hexane/ethyl acetate=5:1) to obtain 2-chloro-4,6-dimethoxyquinoline (0.61 g) as white solids.

Workup

  1. filtrationthe resulting solids were collected by filtration
  2. customThe resulting solids were purified by silica gel column chromatography (hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e7024fce2ba34951a4414402c4d6de8f
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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