Sodium Methoxide → 6-Bromo-3-cyano-2-methoxyquinoline

HRID 986008Notes

Reaction equation

HRID 986008 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([C:13]#[N:14])=[CH:5]2.[CH3:15][O-:16].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:16][CH3:15])[C:6]([C:13]#[N:14])=[CH:5]2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 170398056-Bromo-2-chloroquinoline-3-carbonitrile

Product 1

HCID 142209686-Bromo-3-cyano-2-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-bromo-2-chloro-3-cyano-quinoline (1.2 g) in methanol (30 cm3) was heated under reflux for 16 hours with sodium methoxide [made from sodium (0.116 g) and methanol (20 cm3)]. The mixture was cooled to 0° and the solid filtered to afford 6-bromo-3-cyano-2-methoxyquinoline, m.p. 172°-174°, (0.60 g).

Workup

  1. temperatureThe mixture was cooled to 0°
  2. filtrationthe solid filtered

Sources & evidence

ORD record
ord-10b48fe34e5946eeb3588d7bfce1a5e7
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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