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

HRID 985990Notes

Reaction equation

HRID 985990 reaction equation
C(O/[CH:4]=[CH:5]/[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)=[O:7])C.[OH-].[Na+]>S(=O)(=O)(O)O>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:6](=[O:7])[CH:5]=[CH:4]3)[CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86741910Trans-3-[4-(3-Ethoxypropenamido)phenyl]pyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Trans-3-[4-(3-Ethoxypropenamido)phenyl]pyridine (1.43 g) was stirred in 98% sulphuric acid (4.0 cm3) for 16 hours. The mixture was added to ice (50 g) and the resulting solution was basified to pH8 with 2.5M sodium hydroxide solution. The mixture was extracted with chloroform:methanol, 9:1 (10×100 cm3), and the combined and dried (MgSO4) extracts were concentrated in vacuo to yield a solid which was recrystallised from isopropanol to afford 6-(3-pyridyl)-2-(1H)-quinolone, m.p. 228°-230° (0.39 g).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. dry with materialdried (MgSO4) extracts
  3. concentrationwere concentrated in vacuo
  4. customto yield a solid which
  5. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-2c1135044a1e42489e832afdafdc39ac
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

Loading…