Pyridine → HCID 18510739, compound

HRID 1370254Notes

Reaction equation

HRID 1370254 reaction equation
Cl[N:2]1C(=O)CC[C:3]1=O.N1C=CC=C(C=[O:16])C=1.[C:17](#[N:20])[CH:18]=[CH2:19].C(N(CC)CC)C.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)(Cl)Cl>[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:17]2[CH2:18][CH:19]([C:3]#[N:2])[O:16][N:20]=2)[CH:29]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 7855AcrylonitrileHCID 8471TriethylamineHCID 103713-PyridinecarboxaldehydeHCID 31398Chlorosuccinimide

Product 1

HCID 18510739HCID 18510739, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

) 1-Chloro-2,5-pyrrolidinedione (0.061 mol; 98%) was added portionwise to a mixture of 3-pyridinecarboxaldehyde, oxime (0.041 mol) and pyridine (0.32 ml) in CHCl3 (300 ml) and this mixture was stirred for 3 hours at 40° C. The mixture was cooled to RT. 2-Propenenitrile (0.041 mol) was added. N,N-diethylethanamine (0.061 mol) was added dropwise while the temperature was kept <35° C. The resulting reaction mixture was stirred overnight at RT. The crude mixture was washed with water, then extracted. The organic layer was separated, dried (Na2SO4), filtered and the solvent was evaporated. The residue was purified by two open column chromatography over silica gel ((I) eluent: CH2Cl2/2-propanone 96/4 and CH2Cl2/CH3OH 96/4; (II) hexane/EtOAc 4/1 and CH2Cl2/2-propanone 96/4). The pure fractions were collected and the solvent was evaporated, yielding 5.3 g (74%) of (±)-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarbonitrile (interm. 14)

Workup

  1. temperatureThe mixture was cooled to RT
  2. customwas kept <35° C
  3. customThe resulting reaction mixture
  4. stirringwas stirred overnight at RT
  5. washThe crude mixture was washed with water
  6. extractionextracted
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was purified by two open column chromatography over silica gel ((I) eluent: CH2Cl2/2-propanone 96/4 and CH2Cl2/CH3OH 96/4; (II) hexane/EtOAc 4/1 and CH2Cl2/2-propanone 96/4)
  12. customThe pure fractions were collected
  13. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2b1650377f144f1eab464098e17374e3
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

Loading…