Diethyl Ether → HCID 178419384, compound

HRID 45833Notes

Reaction equation

HRID 45833 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-9525cfac35ac4de1b80c0da753477957
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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