HCID 20270209, compound → HCID 13490360, compound

HRID 485352Notes

Reaction equation

HRID 485352 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:11]=[C:3]2[CH:2]=[O:1])[CH:13]=1

Participants

4

Reactant 1

HCID 20270209HCID 20270209, compound

Product 1

HCID 13490360HCID 13490360, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 3.3 g of 2-hydroxymethyl-N-(3-pyridyl)indole in 33 ml of dry toluene under nitrogen is refluxed with 16.5 g of silver carbonate for 24 hours. Filtration through celite and evaporation yields an oil which is purified by preparative layer chromatography on silica with methylene chloride-ethyl acetate (8:2) as the eluent to yield N-(3-pyridyl)indole-2-carboxaldehyde, m.p. 101°-103° C.

Workup

  1. filtrationFiltration
  2. customthrough celite and evaporation
  3. customyields an oil which
  4. customis purified by preparative layer chromatography on silica with methylene chloride-ethyl acetate (8:2) as the eluent

Sources & evidence

ORD record
ord-5e63a9a291d4429096df2fa08742a8fe
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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