Picolinic acid → HCID 70575142, compound

HRID 1680492Notes

Reaction equation

HRID 1680492 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[NH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]2[NH:24][CH:25]=[CH:26][N:27]=2)=[CH:14]1>O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:10][CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][C:23]2[NH:27][CH:26]=[CH:25][N:24]=2)=[CH:14]1)=[O:9]

Participants

4

Reactant 2

HCID 1018Picolinic acidHCID 70574771HCID 70574771, compound

Product 1

HCID 70575142HCID 70575142, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 2-picolinic acid (0.25 g) and N,N'-carbonyldiimidazole (0.33 g) was heated on a steam bath for 30 minutes in dioxan (10 ml) to give a clear solution. 1-(2-Aminoethyl)-3-(1-imidazolylmethyl) indole (0.48 g) in dioxan (2 ml) was added and the solution was heated on a steam bath for 1 hour and then evaporated. The residue was dissolved in ethyl acetate and the solution was washed with water and dried (NaSO4). Evaporation of the solvent gave a solid which was chromatographed on silica gel. Elution with chloroform gave some impurity and pure product was eluted with a mixture of chloroform and methanol (20:1). Evaporation of the product containing fractions gave a solid which was crystallised from isopropanol/petrol to give 1-[2-(2-picolinoylamino) ethyl]-3-(1-imidazolylmethyl)indole (0.2 g), m.p. 183°-184° C. Found: C, 69.67; H, 5.6; N, 19.42. C20H19N5O requires: C, 69.54; H, 5.55; N, 20.28%.

Workup

  1. customto give a clear solution
  2. temperaturethe solution was heated on a steam bath for 1 hour
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with water
  6. dry with materialdried (NaSO4)
  7. customEvaporation of the solvent
  8. customgave a solid which
  9. customwas chromatographed on silica gel
  10. washElution with chloroform
  11. customgave some impurity and pure product
  12. washwas eluted with a mixture of chloroform and methanol (20:1)
  13. customEvaporation of the product
  14. additioncontaining fractions
  15. customgave a solid which
  16. customwas crystallised from isopropanol/petrol

Sources & evidence

ORD record
ord-fdd6198239d5430ba8face0b51e82d80
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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