Sodium → HCID 14220967, compound

HRID 1904372Notes

Reaction equation

HRID 1904372 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+].[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

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 142210366-Bromo-2-chloro-8-methylquinoline

Product 1

HCID 14220967HCID 14220967, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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. custom]for 24 hours
  2. customThe cooled solution was then evaporated in vacuo
  3. customthe residue was partitioned between chloroform (100 cm3) and water (50 cm3)
  4. extractionThe aqueous phase was further extracted with chloroform (2×50 cm3)
  5. dry with materialdried (MgSO4) organic phases
  6. customwere evaporated in vacuo
  7. customto give a solid which
  8. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-9900d81affdc476294549f9e801400fa
Source dataset
uspto-grants-1989_06
Patent number
US04837334

Reaction notes

Loading…