Sodium Methoxide → 6-Bromo-2-methoxyquinoline

HRID 472157

Reaction equation

HRID 472157 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

2-Chloro-6-bromo-quinoline (142.5 g, 0.6 mol; European Journal of Medicinal Chemistry, 35(10), 931-940; 2000; colourless crystals m.p.: 99.8-101.4° C.) was dissolved in methanol (700 mL), then sodium methoxide (43.9 g; 0.8 mmol) was added and the resulting reaction mixture was refluxed for 16 hours. The reaction mixture was cooled at r.t. and poured in ice-water (1.8 L), the titled product precipitated as a cream solid (133 g, 95%), melting at 157.9-161.1° C. C10H8BrNO2, MW: 238.09. MS (ESI) m/z: 239 (M+1). 1H-NMR (200 MHz, CDCl3) ppm: 4.06 (s, 3H), 6.91 (d, 1H), 7.64-7.75 (m, 2H), 7.88 (d, 2H).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 16 hours
  3. customthe titled product precipitated as a cream solid (133 g, 95%), melting at 157.9-161.1° C

Sources & evidence

ORD record
ord-c2f123d47cd243f3bf676a152df9fb3d
Source dataset
uspto-grants-2014_01
Patent number
US08633208B2

Linked notes

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