Ethyl Bromide → 7-Ethoxy-2-methylquinoline

HRID 339049Notes

Reaction equation

HRID 339049 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][CH3:21]>CN1C(=O)CCC1>[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)[CH3:21]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 1354519692-Methylquinolin-7-ol

Product 1

HCID 867075387-Ethoxy-2-methylquinolineYield 88.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred mixture of 2-methylquinolin-7-ol (400 mg, 2.51 mmol), Cs2CO3 (2.46 g, 7.54 mmol) and NMP (12 mL) was added bromoethane (0.563 mL, 7.54 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 5:1 hexanes:EtOAc) to give 7-ethoxy-2-methylquinoline (416 mg, 88%).

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 5:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-10c8578d969a46b094202a0b360964fb
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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