Pyridine → 1H-Indole-6-carboxaldehyde

HRID 351595

반응식

HRID 351595 반응식
[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

참가 물질

7

반응물 3

HCID 1049PyridineHCID 851461H-indole-6-carbonitrileHCID 178527019HCID 178527019, 화합물

생성물 1

HCID 27734351H-Indole-6-carboxaldehyde수율 89%

시약·촉매·용매 3

HCID 935Nickel촉매HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
45 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f783d89b2e94c15bce37332941c245c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743785B2

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