1-Phenyl-1-propanone → HCID 22477574, compound

HRID 1756110Notes

Reaction equation

HRID 1756110 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8]N)=[N:6][CH:7]=1.[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH2:11][CH3:12]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:11]([CH3:12])=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 71481-Phenyl-1-propanoneHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 22477574HCID 22477574, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Bromo-2-hydrazinopyridine (15.6 g, 0.083 mol) and propiophenone (11.1 ml) was heated at 90° C. (steam bath) for 30 min. Then toluene (100 ml) was added and the resulting solution was refluxed for 2 h to remove water by azeotropic distillation (Dean Stark apparatus). Evaporation of solvent gave 26.4 g of crude product, assumed to be the desired hydrazone. Crude hydrazone (3.02 g) was dissolved in diethylene glycol (30 ml) and heated at 245° C. under argon for 24 h. The reaction mixture was poored crushed ice and extracted with methylene chloride. Drying over MgSO4 and evaporation of solvent left a tary residue which was triturated with diethyl ether to produce 0.84 g (30%) of a brownish, semi-crystalline product.

Workup

  1. temperaturethe resulting solution was refluxed for 2 h
  2. customto remove water
  3. distillationby azeotropic distillation (Dean Stark apparatus)
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-693c9715c94a475e9142d9c5cdaef3f1
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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