3-Methyl-2-butanone → HCID 57426219, compound

HRID 1696404Notes

Reaction equation

HRID 1696404 reaction equation
[CH3:1][C:2]([CH:4]([CH3:6])[CH3:5])=O.Cl.[N+:8]([C:11]1[CH:12]=[C:13]([NH:17][NH2:18])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].O.O.O.C([O-])(=O)C.[Na+]>O.CCO>[N+:8]([C:11]1[CH:12]=[C:13]([NH:17]/[N:18]=[C:2](/[CH:4]([CH3:6])[CH3:5])\[CH3:1])[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 112513-Methyl-2-butanoneHCID 54642853-Nitrophenylhydrazinium(1+) chlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 57426219HCID 57426219, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of isopropyl methyl ketone (2.5 g, 29 mol), 3-nitrophenylhydrazine hydrochloride (6.1 g, 32 mmol) and sodium acetate trihydrate (4.8 g, 35 mmol) in H2O (50 mL) and EtOH (50 mL) was stirred at 80° C. for 1 h. The reaction mixture was cooled and then concentrated under reduced pressure. The residue was partitioned between saturated aqueous NaHCO3 (100 mL) and CHCl3 (150 mL). The organic layer was removed and the aqueous phase was further extracted with CHCl3 (100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=222 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between saturated aqueous NaHCO3 (100 mL) and CHCl3 (150 mL)
  4. customThe organic layer was removed
  5. extractionthe aqueous phase was further extracted with CHCl3 (100 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3add59e608464826bdab79e13bdc5657
Source dataset
uspto-grants-2012_04
Patent number
US08163752B2

Reaction notes

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