Sodium Hydroxide → 6-(3-pyridyl)-2-(1H)-quinolone

HRID 985987Notes

Reaction equation

HRID 985987 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:9]=2)[N:4]=1.[OH-].[Na+]>Br>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][C:3](=[O:2])[CH:12]=[CH:11]3)[CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 142209722-Methoxy-6-(3-pyridyl)quinoline

Product 1

HCID 99910956-(3-pyridyl)-2-(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A stirred solution of 2-methoxy-6-(3-pyridyl) quinoline (1.83 g) in 48% aqueous hydrobromic acid (6 cm3) was heated at 100° C. for 1.5 hours. The mixture was then cooled in an ice bath, adjusted with 5M sodium hydroxide solution to pH 8, and continuously extracted with chloroform for 6 hours. The dried (MgSO4) organic extract was then evaporated to give a solid which was recrystallised from methanol-ethyl acetate to afford 6-(3-pyridyl)-2-[1H]-quinolone, m.p. 217°-218°, (0.62 g).

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. extractioncontinuously extracted with chloroform for 6 hours
  3. dry with materialThe dried (MgSO4)
  4. extractionorganic extract
  5. customwas then evaporated
  6. customto give a solid which
  7. customwas recrystallised from methanol-ethyl acetate

Sources & evidence

ORD record
ord-ff9b2607d9a947969453850003a6e5b4
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

Loading…