Sodium Hydroxide → 8-methyl-6-(3-pyridyl)-2-(1H)-quinolone

HRID 985988Notes

Reaction equation

HRID 985988 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([CH3:19])[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+]>Cl>[CH3:19][C:6]1[CH:7]=[C:8]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:9]=[C:10]2[C:5]=1[NH:4][C:3](=[O:2])[CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 142209862-Methoxy-8-methyl-6-(3-pyridyl)quinoline

Product 1

HCID 138361888-methyl-6-(3-pyridyl)-2-(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 2-methoxy-8-methyl-6-(3-pyridyl)quinoline (1.07 g) in 5M hydrochloric acid (10 cm3) was heated under reflux for 2.5 hours and then cooled. The cooled solution was basified to pH 9 with 2M aqueous sodium hydroxide, extracted with chloroform:methanol 9:1 (4×100 cm3), and the combined and dried (MgSO4) extracts were concentrated in vacuo to afford a solid. Recrystallisation of the solid from ethyl acetate-methanol gave 8-methyl-6-(3-pyridyl)-2-(1H)-quinolone, m.p. 235.5°-236.5°, (0.63 g).

Workup

  1. temperatureunder reflux for 2.5 hours
  2. temperaturecooled
  3. extractionextracted with chloroform:methanol 9:1 (4×100 cm3)
  4. dry with materialdried (MgSO4) extracts
  5. concentrationwere concentrated in vacuo
  6. customto afford a solid
  7. customRecrystallisation of the solid from ethyl acetate-methanol

Sources & evidence

ORD record
ord-e925963f774547ba954971c20cfb8e0b
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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