Acetic Acid → 5-(2,5-Dimethyl-1H-pyrrol-1-yl)-2-ethylpyridine

HRID 850108ノート

反応式

HRID 850108 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1)[CH3:2].[CH3:10][C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15].C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:15][C:14]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[N:4][CH:5]=2)[C:11]([CH3:10])=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 138607296-Ethylpyridin-3-amine

生成物 1

HCID 193659555-(2,5-Dimethyl-1H-pyrrol-1-yl)-2-ethylpyridine収率 46%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 2-ethylpyridin-5-amine (3.2 g, 26 mmol), 2,5-hexanedione (3.0 g, 26 mmol) and acetic acid (1 ml) in toluene (50 ml) was heated under reflux for 24 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane (50 ml) and water (20 ml). The aqueous phase was basified with aqueous sodium hydroxide (2M) and then extracted with dichloromethane (50 ml). The extract was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica by elution with dichloromethane/methanol (95:5) to give the title compound (2.38 g, 46%) as a colourless oil, which was characterised by 1H-N.M.R. spectroscopy.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between dichloromethane (50 ml) and water (20 ml)
  5. extractionextracted with dichloromethane (50 ml)
  6. dry with materialThe extract was dried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica by elution with dichloromethane/methanol (95:5)

出典と根拠

ORDレコード
ord-e580e35336ec4bcea097118f63c6beec
出典データセット
uspto-grants-2000_01
特許番号
US06015825

反応ノート

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