Hydrogen Peroxide → HCID 178468764, compound

HRID 1034440Notes

Reaction equation

HRID 1034440 reaction equation
OO.[C:3]([O:8][CH2:9][CH3:10])(=[O:7])[C:4]([CH3:6])=O.[CH2:11]([C:13]1[NH:22][C:16]2=[N:17]C=[CH:19][C:20](C)=[C:15]2[N:14]=1)[CH3:12].O.O.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O.[Na+].[Na+].[Na+].C(=O)(O)[O-].[Na+]>O.S(=O)(=O)(O)O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[CH2:11]([C:13]1[NH:22][C:16]2=[N:17][C:4]([C:3]([O:8][CH2:9][CH3:10])=[O:7])=[CH:6][C:20]([CH3:19])=[C:15]2[N:14]=1)[CH3:12]

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 12041Ethyl pyruvateHCID 71474Sodium Citrate DihydrateHCID 516892Sodium BicarbonateHCID 178437450HCID 178437450, compound

Product 1

HCID 178468764HCID 178468764, compound

Reagents, catalysts & solvents 3

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

Hydrogen peroxide (30% w/w in water; 14 ml) was added dropwise to stirred and cooled (-10° C.) ethyl pyruvate (22 ml). This mixture and a solution of iron (II) sulphate heptahydrate (37.5 g) in water (45 ml) were added simultaneously, dropwise into a stirred and cooled (-10° C.) solution of 2-ethyl-7-methyl-3H-imidazo[4,5-b]pyridine (7.1 g) in water (23 ml) and concentrated sulphuric acid (7.5 ml). The mixture was then poured onto ice and trisodium citrate dihydrate (40 g) was added. The mixture was neutralised with solid sodium bicarbonate and partitioned between chloroform (×3) and water. The organic phases were combined, dried and evaporated. Column chromatography eluting with 10% methanol in ether gave a brown solid which was triturated with ether to give the title compound as a pale yellow solid (1.9 g), m.p. 151°-153° C.

Workup

  1. stirringdropwise into a stirred
  2. additionwas added
  3. custompartitioned between chloroform (×3) and water
  4. customdried
  5. customevaporated
  6. washColumn chromatography eluting with 10% methanol in ether
  7. customgave a brown solid which
  8. customwas triturated with ether

Sources & evidence

ORD record
ord-671954d19dfb4d26a90abb69fbf45d32
Source dataset
uspto-grants-1994_05
Patent number
US05317023

Reaction notes

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