Water → HCID 70983053, compound

HRID 338873Notes

Reaction equation

HRID 338873 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1.[C:14]([O-])([O-])=O.[Cs+].[Cs+].IC.O>CN1C(=O)CCC1>[Br:1][C:2]1[C:11]([O:12][CH3:14])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 21824657HCID 21824657, compound

Product 1

HCID 70983053HCID 70983053, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 7-bromo-2-methylquinolin-8-ol (4.10 g, 14.64 mmol) and Cs2CO3 (11.92 g, 36.59 mmol) in NMP (20 mL) was added iodomethane (1.01 mL, 16.10 mmol) at 0° C. The reaction was warmed to ambient temperature and stirred at ambient temperature for 40 minutes. Water (30 mL) was and added and extracted with DCM (30 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (DCM) to give 7-bromo-8-methoxy-2-methylquinoline (3.62 g, 91.23%) as an oil.

Workup

  1. additionadded
  2. extractionextracted with DCM (30 mL)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (DCM)

Sources & evidence

ORD record
ord-9ba32009769b46189d5d7c3111f9c466
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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