Hydrochloric Acid → HCID 57940657, compound

HRID 1437212Notes

Reaction equation

HRID 1437212 reaction equation
[Li].[CH2:2]([O:4][C:5](=[O:18])[C:6](=O)[CH:7]([CH3:16])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O)[CH3:3].Cl.[NH:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[NH2:21].[OH-].[Na+]>C(O)C>[CH2:2]([O:4][C:5]([C:6]1[C:7]([CH3:16])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[N:21]=1)=[O:18])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3028194LithiumHCID 10728727HCID 10728727, compoundHCID 109095193-Hydrazinopyridine

Product 1

HCID 57940657HCID 57940657, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The above-obtained lithium salt of 3-methyl-4-phenyl-2,4-dioxobutanoic acid ethyl ester (1.502 g) was dissolved in ethanol (30 mL). To the resultant mixture were added 1M HCl in ethanol (8 mL) and 3-hydrazinopyridine (1.977 g) obtained from Referential Example 52, followed by refluxing for 2.5 hours. The mixture was cooled in air. The reaction mixture was alkalinized to pH 10 with an aqueous solution of sodium hydroxide. The mixture was partitioned between chloroform and water. The aqueous layer was extracted with chloroform. The organic layer was washed with saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-acetone), to thereby give the title compound as an oily substance (1.428 g, 34%).

Workup

  1. temperatureby refluxing for 2.5 hours
  2. temperatureThe mixture was cooled in air
  3. customThe mixture was partitioned between chloroform and water
  4. extractionThe aqueous layer was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate anhydrate
  7. filtrationfollowed by filtration
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (chloroform-acetone)

Sources & evidence

ORD record
ord-07283153f8c649aba910af3e2701fea2
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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