Cesium carbonate → 7-(2-Methoxyethoxy)-2-methylquinoline

HRID 339050Notes

Reaction equation

HRID 339050 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH2:21][O:22][CH3:23]>CN1C(=O)CCC1>[CH3:23][O:22][CH2:21][CH2:20][O:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 1354519692-Methylquinolin-7-ol

Product 1

HCID 709831307-(2-Methoxyethoxy)-2-methylquinolineYield 57.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred mixture of 2-methylquinolin-7-ol (300 mg, 1.88 mmol), Cs2CO3 (1.84 g, 5.65 mmol) and NMP (10 mL) was added 1-bromo-2-methoxyethane (0.786 g, 5.65 mmol). The reaction mixture was stirred at ambient temperature overnight. The reaction was partitioned between ether and water. The aqueous layer was extracted with ether. The combined organic layers were washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (2:1 to 1:2 hexanes/EtOAc) to give 7-(2-methoxyethoxy)-2-methylquinoline (235 mg, 57%).

Workup

  1. customThe reaction was partitioned between ether and water
  2. extractionThe aqueous layer was extracted with ether
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (2:1 to 1:2 hexanes/EtOAc)

Sources & evidence

ORD record
ord-973b3d4e4cef4e76918d0d68603c263c
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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