Water → 8-Chloro-6-methoxyquinoline

HRID 2241965Notes

Reaction equation

HRID 2241965 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:13]([O-])([O-])=O.[K+].[K+].IC.O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 207011698-Chloroquinolin-6-ol

Product 1

HCID 207011688-Chloro-6-methoxyquinolineYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.3 g of 8-chloro-6-hydroxyquinoline (Step 1, 3.3 g) in dimethylformamide was added K2CO3 (3.8 g), followed by iodomethane (5.2 g). The mixture was stirred at room temperature overnight. Water was then added and the aqueous mixture was extracted with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using 100% CH2Cl2, to give 2.2 g of the desired product as a beige solid; MP=74-75° C.; MS (ES) m/z (relative intensity): 194 (M+H)+ (100).

Workup

  1. extractionthe aqueous mixture was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated on a rotary evaporator
  5. customThe crude product was purified by flash chromatography on silica gel using 100% CH2Cl2

Sources & evidence

ORD record
ord-290954727a2c465487a8fae208271f78
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

Loading…