Sodium Methoxide → 4-Bromo-7-chloro-2-methoxyquinoline

HRID 2090051Notes

Reaction equation

HRID 2090051 reaction equation
[CH3:1][O-:2].[Na+].Br[C:5]1[CH:14]=[C:13]([Br:15])[C:12]2[C:7](=[CH:8][C:9]([Cl:16])=[CH:10][CH:11]=2)[N:6]=1>CO>[Br:15][C:13]1[C:12]2[C:7](=[CH:8][C:9]([Cl:16])=[CH:10][CH:11]=2)[N:6]=[C:5]([O:2][CH3:1])[CH:14]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58349489HCID 58349489, compound

Product 1

HCID 583494734-Bromo-7-chloro-2-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.5 M in MeOH, 2.0 mL, 1.0 mmol) was added to a solution of 2,4-dibromo-7-chloroquinoline (341 mg, 1.06 mmol) in MeOH (7 mL). The mixture was refluxed for one hour then cooled to room temperature. The resulting precipitate was collected by filtration to afford the title compound as an off-white solid: 1H NMR (500 MHz, CDCl3): δ 8.00 (d, J=8.8 Hz, 1H); 7.85 (d, J=2.1 Hz, 1H); 7.40 (dd, J=8.8, 2.1 Hz, 1H); 7.22 (s, 1H); 4.04 (s, 3H); LC4 2.45 min. (M+H)=274.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-7d622a139c7647c5934383c2b122158b
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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