Hexanal → 3-Butylimidazo[1,2-a]pyridine-6-carboxylic acid

HRID 14236

反応式

HRID 14236 の反応式
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1>C(O)(C)C.O>[CH2:3]([C:2]1[N:10]2[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[CH:16]=[CH:17][C:9]2=[N:8][CH:1]=1)[CH2:4][CH2:5][CH3:6]

参加物

4

反応物 2

HCID 6184HexanalHCID 184966-Aminonicotinic acid

生成物 1

HCID 210857313-Butylimidazo[1,2-a]pyridine-6-carboxylic acid収率 11.9%

試薬・触媒・溶媒 1

HCID 21889133Propan-2-ol--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

To hexanal (1.02 g, 10.2 mmol) in 15 mL of isopropyl alcohol-water (4:1 v/v) was added CuCl2 (1.37 g, 10.2 mmol). The mixture was heated at 80° C. for 2.5 h, then cooled. The solids were removed by filtration and the filtrate was added to 6-aminonicotinic acid (1.35 g, 10 mmol). The mixture was stirred overnight at room temperature, then heated at reflux 32 h. After cooling, the solvents were removed under reduced pressure and MeOH was added to the residue. The resulting solid was removed by filtration and the filtrate was concentrated to dryness. MeOH was again added, and the resulting solid removed by filtration. After concentration of the filtrate, the residue was chromatographed on silica gel using MeOH-dichloromethane (33/67) to give 0.26 g of 3-butylimidazo[1,2-a]pyridine-6-carboxylic acid.

後処理

  1. temperaturecooled
  2. customThe solids were removed by filtration
  3. temperatureheated
  4. temperatureat reflux 32 h
  5. temperatureAfter cooling
  6. customthe solvents were removed under reduced pressure and MeOH
  7. additionwas added to the residue
  8. customThe resulting solid was removed by filtration
  9. concentrationthe filtrate was concentrated to dryness
  10. additionMeOH was again added
  11. customthe resulting solid removed by filtration
  12. customAfter concentration of the filtrate, the residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-67a4f68931c34afa8b6e232c4a21c8db
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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