Sodium Methoxide → HCID 14220967, compound

HRID 568385Notes

Reaction equation

HRID 568385 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[CH:5]2.[CH3:14][O-:15].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]=[C:7]([O:15][CH3:14])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 142210366-Bromo-2-chloro-8-methylquinoline

Product 1

HCID 14220967HCID 14220967, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-bromo-2-chloro-8-methylquinoline (10.7 g) in methanol (80 cm3) was heated under reflux with a solution of sodium methoxide [made from sodium (2.76 g) in methanol (50 cm3)] for 24 hours. The cooled solution was then evaporated in vacuo and the residue was partitioned between chloroform (100 cm3) and water (50 cm3). The aqueous phase was further extracted with chloroform (2×50 cm3) and the combined and dried (MgSO4) organic phases were evaporated in vacuo to give a solid which was recrystallised from ethyl acetate:hexane, 1:9, to afford 6-bromo-2-methoxy-8-methylquinoline, m.p. 89°-91° (8.3 g).

Workup

  1. customThe cooled solution was then evaporated in vacuo
  2. customthe residue was partitioned between chloroform (100 cm3) and water (50 cm3)
  3. extractionThe aqueous phase was further extracted with chloroform (2×50 cm3)
  4. dry with materialdried (MgSO4) organic phases
  5. customwere evaporated in vacuo
  6. customto give a solid which
  7. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-f595c9dd513341c196ba5a271675b279
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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