3-Bromoquinoline → 3-Methoxyquinoline

HRID 747335

Reaction equation

HRID 747335 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:12][O-:13].[Na+]>CN(C=O)C>[CH3:12][O:13][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 214133-BromoquinolineHCID 10942334Sodium Methoxide

Product 1

HCID 5758073-MethoxyquinolineYield 6.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-bromoquinoline (22.54 g, 108 mmol) in anhydrous DMF (110 mL) was treated with sodium methoxide (11.70 g, 217 mmol) and stirred at 80° C. for 16 hours. The reaction mixture was then concentrated and the residue taken up in ethyl acetate (300 mL) and water (60 mL). The organic phase was separated, washed with brine (2×60 mL), dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (ethyl acetate/hexane; 1:3) to give 3-methoxyquinoline (1.06 g, 6%). 1H NMR (CDCl3) δ 3.95 (s, 3H), 7.38 (d, 1H, J=1.5 Hz), 7.54 (m, 2H), 7.72 (d, 1H, J=7.5 Hz), 8.04 (d, 1H, J=7.5 Hz), 8.67 (d, 1H, J=1.5 Hz).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customThe organic phase was separated
  3. washwashed with brine (2×60 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica gel (ethyl acetate/hexane; 1:3)

Sources & evidence

ORD record
ord-eccdd586c3f04ad1b57a3171690ac408
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

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