Diethyl Ether → HCID 178419384, compound

HRID 1843621Notes

Reaction equation

HRID 1843621 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:10][N:11](C)C)[CH:5]=[CH:6][CH:7]=1.O.[NH2:22]N.C(OCC)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:10][NH:11][N:22]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 67185534HCID 67185534, compound

Product 1

HCID 178419384HCID 178419384, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8 g (0.024 mol) of 1-(3-bromophenyl)-3-(dimethylamino)-2-pyridin-4-ylprop-2-en-1-one were dissolved in 20 ml of ethanol and 3 mL (0.06 mol) of hydrazine hydrate were added. The solution was refluxed under stirring for 4 hours. The title compound was collected by filtration. The filtrate was evaporated, the residue taken up with dichloromethane and washed with water. The organic layer, dried over Na2SO4, was evaporated to dryness and triturated with diethylether affording a second crop of the title compound (7.2 g overall; 100% yield).

Workup

  1. temperatureThe solution was refluxed
  2. filtrationThe title compound was collected by filtration
  3. customThe filtrate was evaporated
  4. washwashed with water
  5. dry with materialThe organic layer, dried over Na2SO4
  6. customwas evaporated to dryness

Sources & evidence

ORD record
ord-76c7ab9476144904862330d530ea8574
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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