Pyridine → 1H-Indole-6-carboxaldehyde

HRID 351595

反応式

HRID 351595 の反応式
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1)#N.[PH2]([O-])=[O:13].[Na+].N1C=CC=CC=1>O.C(O)(=O)C.[Ni]>[NH:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([CH:1]=[O:13])[CH:11]=2)[CH:7]=[CH:8]1

参加物

7

反応物 3

HCID 1049PyridineHCID 851461H-indole-6-carbonitrileHCID 178527019HCID 178527019、化合物

生成物 1

HCID 27734351H-Indole-6-carboxaldehyde収率 89%

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
45 °C

実験手順

To a solution of 6-cyanoindole (15.0 g) and sodium hypophosphite (90 g) in water (326 mL), acetic acid (326 mL), and pyridine (652 mL) was added Raney Nickel catalyst and the mixture stirred at 45° C. for 45 minutes. The mixture was filtered through Celite and the filtrate extracted with ethyl acetate (3×500 mL). The extracts were dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was crystallized from a mixture of dichloromethane and hexanes to provide 13.6 g (89%) of the title compound.

後処理

  1. filtrationThe mixture was filtered through Celite
  2. extractionthe filtrate extracted with ethyl acetate (3×500 mL)
  3. dry with materialThe extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was crystallized from a mixture of dichloromethane and hexanes

出典と根拠

ORDレコード
ord-5f783d89b2e94c15bce37332941c245c
出典データセット
uspto-grants-2004_06
特許番号
US06743785B2

関連ノート

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