Sodium Methoxide → 6-Bromo-2-methoxyquinoline

HRID 568354

Reaction equation

HRID 568354 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[N:3]=1.[CH3:13][O-:14].[Na+]>CO>[Br:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([O:14][CH3:13])[CH:11]=[CH:10]2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 128940866-Bromo-2-chloroquinoline

Product 1

HCID 106575386-Bromo-2-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-6-bromoquinoline (4.0 g) in methanol (20 cm3) was heated under reflux with sodium methoxide [made from sodium (0.5 g) and methanol (20 cm3)] for 16 hours. The solvent was removed in vacuo and the residue was partitioned, between water (20 cm3) and chloroform (100 cm3). The aqueous phase was extracted wth chloroform (2×30 cm3) and the dried (MgSO4) organic extracts were evaporated to give a solid which was recrystallised from petroleum ether (b.p. 60°-80°) to yield the title compound, m.p. 93°-96°, (3.0 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned, between water (20 cm3) and chloroform (100 cm3)
  3. extractionThe aqueous phase was extracted wth chloroform (2×30 cm3)
  4. dry with materialthe dried (MgSO4) organic extracts
  5. customwere evaporated
  6. customto give a solid which
  7. customwas recrystallised from petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-80bb0d7044fe4160bd24da6454bc31de
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Linked notes

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