2-Methyl-1-(3-nitrophenyl)-1-propanone → 2-Methyl-1-(3-nitrophenyl)-1-propanone hydrazone

HRID 428937ノート

反応式

HRID 428937 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 598980482-Methyl-1-(3-nitrophenyl)-1-propanone hydrazone

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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 nmuol). 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 cluting with dichloromethane:ethyl acetate (19:1) to give the title compound as a mixture of cis and trans hydazones (0.54 g, 50%).

後処理

  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 cluting with dichloromethane:ethyl acetate (19:1)

出典と根拠

ORDレコード
ord-bd78f6503b0c47e1b886e1148d54d7b6
出典データセット
uspto-grants-2001_11
特許番号
US06313312B1

反応ノート

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