Water → N-[3-(1-Hydroxyhexyl)phenyl]pyridine-2-carboxamide

HRID 414841ノート

反応式

HRID 414841 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)=[O:2].[CH2:18]([Mg]Br)[CH2:19][CH2:20][CH2:21][CH3:22].O>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 962WaterHCID 14349158N-(3-formyl-phenyl)pyridine-2-carboxamideHCID 178445865HCID 178445865、化合物

生成物 1

HCID 14349159N-[3-(1-Hydroxyhexyl)phenyl]pyridine-2-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

The aldehyde (1.1 g) was dissolved in dry tetrahydrofuran, and cooled in an ice bath. To this cold solution was added dropwise, a solution of pentylmagnesium bromide (prepared from 1-bromopentane (1.9 g) and magnesium turnings (0.31 g) in dry ether). The reaction mixture was stirred at 0° C. for two hours, allowed to warm to room temperature and was carefully poured into cold water. The aqueous solution was extracted with ethyl acetate, and the organic extract was washed with aqueous ammonium chloride solution, brine and then dried over anhydrous magnesium sulfate. All volatilss were removed to leave a viscous liquid which quickly solidified on standing. This solid was crystallized from ethyl acetate/hexane to give pure product.

後処理

  1. temperaturecooled in an ice bath
  2. additionTo this cold solution was added dropwise
  3. temperatureto warm to room temperature
  4. extractionThe aqueous solution was extracted with ethyl acetate
  5. extractionthe organic extract
  6. washwas washed with aqueous ammonium chloride solution, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAll volatilss were removed
  9. customto leave a viscous liquid which
  10. customThis solid was crystallized from ethyl acetate/hexane
  11. customto give pure product

出典と根拠

ORDレコード
ord-9abddd054c324cc0bb4643993a02d356
出典データセット
uspto-grants-1988_12
特許番号
US04794188

反応ノート

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