Sodium Hydroxide → HCID 19867081, compound

HRID 1904361Notes

Reaction equation

HRID 1904361 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH2:12][CH2:11]3)[CH:4]=[C:5]([CH3:7])[N:6]=1.[Br:19]Br.[OH-].[Na+]>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:19][C:16]1[CH:17]=[C:8]([N:3]2[CH:4]=[C:5]([CH3:7])[N:6]=[C:2]2[CH3:1])[CH:9]=[C:10]2[C:15]=1[NH:14][C:13](=[O:18])[CH2:12][CH2:11]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 19867070HCID 19867070, compound

Product 1

HCID 19867081HCID 19867081, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 6-(2,4-dimethylimidazol-1-yl)-3,4-dihydro-2-(1H)-quinolone (0.2 g) in concentrated sulphuric acid (5 cm3) was added bromine (0.045 cm3) and silver sulphate (0.186 g). The mixture was stirred at room temperature for 16 hours, poured onto ice (20 g.) and the mixture brought to pH 10 with aqueous 5M sodium hydroxide solution and extracted with dichloromethane (100 cm3). The organic extract was dried (MgSO4), filtered and evaporated in vacuo to yield a white solid. This solid was recrystallised from ethyl acetate to give 8-bromo-6-(2,4-dimethylimidazol-1-yl)-3,4-dihydro-2-(1H)-qu (0.15 g), m.p. 242°.

Workup

  1. additionpoured onto ice (20 g.)
  2. extractionextracted with dichloromethane (100 cm3)
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto yield a white solid
  8. customThis solid was recrystallised from ethyl acetate
  9. customto give 8-bromo-6-(2,4-dimethylimidazol-1-yl)-3,4-dihydro-2-(1H)-qu (0.15 g), m.p. 242°

Sources & evidence

ORD record
ord-01285c0a59aa478f8525e1cf713d2592
Source dataset
uspto-grants-1989_06
Patent number
US04837334

Reaction notes

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