2-Methyl-1-(3-nitrophenyl)-1-propanone → HCID 59898048, compound

HRID 1826447Notes

Reaction equation

HRID 1826447 reaction equation
[CH3:1][CH:2]([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.O.O.[NH2:17][NH2:18]>O>[CH3:1][CH:2]([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=[N:17][NH2:18]

Participants

4

Reactant 2

HCID 149240122-Methyl-1-(3-nitrophenyl)-1-propanoneHCID 22141362Hydrazine--water (1/2)

Product 1

HCID 59898048HCID 59898048, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a partially dissolved solution of 2-methyl-1-(3-nitrophenyl)-1-propanone (Preparation 55, 1.0 g, 5.2 mmol) in industrial methylated spirits (6 ml) was added dropwise hydrazine hydrate monohydrate (0.5 ml, 10.4 mmol). The reaction mixture was refluxed for 16 h, before cooling to room temperature and pouring into ice and water (50:50, 15 ml) giving a very fine white precipitate in a yellow solution. The mixture was extracted with diethyl ether (2×50 ml), the combined organic extracts were washed with brine and dried (MgSO4), before concentrating to give an amber oil. The crude product was purified by chromatography on silica gel eluting with dichloromethane:ethyl acetate (19:1) to give the title compound as a mixture of cis and trans hydazones (0.54 g, 50%).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customgiving a very fine white precipitate in a yellow solution
  3. extractionThe mixture was extracted with diethyl ether (2×50 ml)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationbefore concentrating
  7. customto give an amber oil
  8. customThe crude product was purified by chromatography on silica gel eluting with dichloromethane:ethyl acetate (19:1)

Sources & evidence

ORD record
ord-b7a89c139e2d404f83c20d6adbcd9bc6
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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