Hydrogen Bromide → HCID 14221016, compound

HRID 985997Notes

Reaction equation

HRID 985997 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[C:15]([CH3:21])=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH:9]=[CH:8]2.Br.[OH-].[Na+]>O>[OH:2][C:3]1[CH:4]=[C:5]([C:14]2[C:15]([CH3:21])=[N:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 13836193HCID 13836193, compound

Product 1

HCID 14221016HCID 14221016, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8-methoxy-6-[2,6-dimethylpyrid-3-yl]-2-(1H)-quinolone (0.15 g) and 48% aqueous HBr (5 cm3) was heated under reflux for 19 hours. The mixture was diluted with water (20 cm3), basified to pH7 with 5M sodium hydroxide solution, and extracted with CHCl3 (3×50 cm3). The combined and dried (MgSO4) chloroform extracts were evaporated in vacuo to afford a solid which was recrystallised from ethyl acetate to give 8-hydroxy-6-[2,6-dimethylpyrid-3-yl]-2-(1H)-quinolone, m.p. 276°-277°, (0.132 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. extractionextracted with CHCl3 (3×50 cm3)
  4. dry with materialdried (MgSO4) chloroform extracts
  5. customwere evaporated in vacuo
  6. customto afford a solid which
  7. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-f64b69e62b894194ad5be23e875e8fa3
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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