Ethyl ketone → HCID 59443018, compound

HRID 1959152Notes

Reaction equation

HRID 1959152 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:14][CH2:15][C:16](=O)[CH2:17][CH3:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:15]([C:16]1([CH2:17][CH3:18])[NH:6][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=2[O:1]1)[CH3:14]

Participants

6

Reactant 4

HCID 7288Ethyl ketoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 684855612-Hydroxy-4-nitrobenzamide

Product 1

HCID 59443018HCID 59443018, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of the compound obtained in (1) described above (5 g), 3-pentanone (6.6 g) and p-toluenesulfonic acid monohydrate (1.6 g) in toluene (70 mL) was heated under reflux overnight. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate (100 mL) and the mixture was extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was recrystallized from ethyl acetate/dichloromethane (1:1) to give the titled compound (5 g) as a colorless powder.

Workup

  1. additionA suspension of the compound
  2. temperaturewas heated
  3. temperatureunder reflux overnight
  4. extractionthe mixture was extracted with ethyl acetate (100 mL×3)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was recrystallized from ethyl acetate/dichloromethane (1:1)

Sources & evidence

ORD record
ord-3221af00a4b947b79234822007067993
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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