Pyridine → 1H-Indole-6-carboxaldehyde

HRID 983944Notes

Reaction equation

HRID 983944 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 27734351H-Indole-6-carboxaldehydeYield 89%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b8a4db24b9314b3da9f515e627d7bedc
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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