Hydrogen Bromide → 1-Phenyl-2-(pyridin-3-yl)ethan-1,2-dione

HRID 1579118Notes

Reaction equation

HRID 1579118 reaction equation
Cl.[CH2:2]([C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br.[OH2:18]>CS(C)=O>[C:3]1([C:2]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[O:18])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 21558184Benzyl-(3-pyridyl)-ketone-hydrochloride

Product 1

HCID 109875561-Phenyl-2-(pyridin-3-yl)ethan-1,2-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

23.4 g (0.1 mol) of benzyl-(3-pyridyl)-ketone-hydrochloride are taken up in 180 ml of dimethyl sulphoxide and the solution is treated with 20 ml of 48% hydrobromic acid. The reaction mixture is stirred for 18 hours at 80° - 85°C and subsequently poured on a mixture of 800 g of ice and 1000 ml of water. The yellow emulsion is extracted with 2 × 200 ml of ethyl acetate. The two organic phases are combined, washed with water and dried over sodium sulphate. The red solution is concentrated in a rotary evaporator until a residual oil is left which is distilled in a bulb tube at 140° - 150°C/0.1 Torr (m.p. 56° - 57°C).

Workup

  1. extractionThe yellow emulsion is extracted with 2 × 200 ml of ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationThe red solution is concentrated in a rotary evaporator until a residual oil
  5. waitis left which
  6. distillationis distilled in a bulb tube at 140° - 150°C/0.1 Torr (m.p. 56° - 57°C)

Sources & evidence

ORD record
ord-e45a5ce9e6f745799c42c59104dfb605
Source dataset
uspto-grants-1976_02
Patent number
US03940486

Reaction notes

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