Diethyl Ether → HCID 59327640, compound

HRID 538750Notes

Reaction equation

HRID 538750 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[C:9]([NH:11][NH:12][C:13](=[O:18])[CH2:14][C:15](=O)[CH3:16])=[O:10])=[CH:4][CH:3]=1.[NH2:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29]C=CC=1)=O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S([C:52](F)(F)F)(=O)=O.[CH2:56](OCC)[CH3:57]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:20])([CH3:19])[C:9]([NH:11][NH:12][C:13]([C:14]2[C:56]([CH3:57])=[N:21][C:22]3[C:16]([C:15]=2[CH3:52])=[CH:29][CH:30]=[CH:25][CH:23]=3)=[O:18])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11952PhenacylamineHCID 2733225Ytterbium triflateHCID 59327641HCID 59327641, compound

Product 1

HCID 59327640HCID 59327640, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N′-(2-(4-chlorophenyl)-2-methylpropanoyl)-3-oxobutanehydrazide (1.77 g, 6.0 mmol) in ethanol (15 ml) was added 2-aminoacetophenone (0.61 ml, 5.0 mmol) followed by ytterbium triflate (310 mg, 0.5 mmol). The mixture was heated at 70° C. for 12 hours, cooled to room temperature, and the ethanol was removed under reduced pressure. The crude residue was dissolved in ethyl acetate, poured into a separatory funnel, and washed with water (2×), saturated sodium bicarbonate, and brine. The organic phase was separated, and solvent removed under reduced pressure, to provide a viscous oil, which solidified upon the addition of ethyl ether. The solid was filtered off and washed with diethyl ether, to provide N′-(2-(4-chlorophenyl)-2-methylpropanoyl)-2,4-dimethylquinoline-3-carbohydrazide (1.8 g, 91%) as a light yellow powder. TLC Rf=0.44 using 100% ethyl acetate eluent on a glass backed silica gel plate.

Workup

  1. temperaturecooled to room temperature
  2. customthe ethanol was removed under reduced pressure
  3. dissolutionThe crude residue was dissolved in ethyl acetate
  4. additionpoured into a separatory funnel
  5. washwashed with water (2×), saturated sodium bicarbonate, and brine
  6. customThe organic phase was separated
  7. customsolvent removed under reduced pressure
  8. customto provide a viscous oil, which
  9. filtrationThe solid was filtered off
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-59368039f91348ec961cd49117c8c96e
Source dataset
uspto-grants-2014_10
Patent number
US08865739B2

Reaction notes

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