3-Acetylpyridine → 1-(3-Pyridinyl)-1-ethanone hydrazone
Reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)(=O)[CH3:2].O.O.[NH2:12][NH2:13]>O>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[N:12][NH2:13])[CH3:2])[CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 3-acetylpyridine (6.1 g, 52 mmol) in industrial methylated spirits (50 ml) was added dropwise hydrazine hydrate monohydrate (3.11 ml, 0.1 mol). The reaction mixture was refluxed for 4 h, before cooling to room temperature and stirring for 16 h. Water (25 ml) was added and the volatile organics were removed in vacuo. The predominantly aqueous residual liquor was extracted with ethyl acetate, and the combined organic extracts were dried (Na2SO4) and concentrated to give a yellow oil (5.4 g, 80%) which was taken forward without further purification.
Workup
- temperatureThe reaction mixture was refluxed for 4 h
- customthe volatile organics were removed in vacuo
- extractionThe predominantly aqueous residual liquor was extracted with ethyl acetate
- dry with materialthe combined organic extracts were dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-038c360d8d524b7cae77a7c6c57cefe8
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313312B1
Reaction notes
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