4-Chloro-6,7-dimethoxyquinoline → HCID 135742189, compound

HRID 2115784Notes

Reaction equation

HRID 2115784 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14]C)=[C:9]([O:12]C)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.Cl.[NH+]1C=CC=CC=1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([OH:12])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium BicarbonateHCID 21584435Pyridinium hydrochloride

Product 1

HCID 135742189HCID 135742189, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

In a tube with a stirring bar was introduced 4-chloro-6,7-dimethoxyquinoline (1.5 g, 6.71 mmol) and 15 g of pyridinium hydrochloride. The tube was sealed and the mixture stirred at 200° C. for 1 h. The reaction was cooled to RT and a saturated solution of NaHCO3 was added followed by EtOAc. The EtOAc layer was washed with a saturated solution of NaHCO3, and the aqueous solution was back extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under vacuum. The crude mixture was used in the next step.

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction was cooled to RT
  3. washThe EtOAc layer was washed with a saturated solution of NaHCO3
  4. extractionthe aqueous solution was back extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-73bfe2cf004f49dd8333e559de371cbd
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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