Pyridine → 2-methyl-1H-indole-5-carbaldehyde

HRID 2181186Notes

Reaction equation

HRID 2181186 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]#N)=[CH:6][CH:5]=2.O.[PH2]([O-])=[O:15].[Na+].N1C=CC=CC=1>C(O)(=O)C.[Ni]>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH:11]=[O:15])=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 1049PyridineHCID 118296862-Methyl-1H-indole-5-carbonitrileHCID 178418950HCID 178418950, compound

Product 1

HCID 218655092-methyl-1H-indole-5-carbaldehydeYield 80.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 3.9 g 2-methyl-1H-indole-5-carbonitrile [Journal of Organic Chemistry (1994), 9(21), 6372-7], 7.22 g sodium hypophosphite monohydrate and 2.60 g Raney-Nickel in 110 ml acetic acid (50%)/pyridine 1:1 was stirred at 45° C. for 75 min. After cooling down to room temperature, the reaction mixture was filtered (dicalite), then the filtrate poured into ice-water and extracted 3 times with EtOAc. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated. The residue was crystallized from n-heptane to give 3.19 g of 2-methyl-1H-indole-5-carbaldehyde as light red solid.

Workup

  1. temperatureAfter cooling down to room temperature
  2. filtrationthe reaction mixture was filtered (dicalite)
  3. additionthe filtrate poured into ice-water
  4. extractionextracted 3 times with EtOAc
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was crystallized from n-heptane

Sources & evidence

ORD record
ord-af0f0e3bc4b3489cac65d6e7b29f3b1b
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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