Sodium Methoxide → 6-Bromo-2-methoxyquinoline

HRID 985999Notes

Reaction equation

HRID 985999 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>[CH3:13][O:14][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

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 with chloroform (2×30 cm3) and the dried (MgSO4) extracts were evaporated to give a solid which was recrystallised from petroleum ether (b.p. 60°-80°) to yield 2-methoxy-6-bromoquinoline, 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 with chloroform (2×30 cm3)
  4. dry with materialthe dried (MgSO4) 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-ffea307a3b4a455b9a3563f24947804e
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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