5-Nitro-2-(1-pyrrolidinyl)pyridine → 6-(Pyrrolidin-1-yl)pyridin-3-amine

HRID 413269

Reaktionsgleichung

Reaktionsgleichung von HRID 413269
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+].Cl.CCOCC>CO.[OH-].[Pd+2].[OH-]>[N:10]1([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

6

Edukt 3

HCID 3168235-Nitro-2-(1-pyrrolidinyl)pyridineHCID 2723923Ammonium formateHCID 10953452Ether hydrochloride

Produkt 1

HCID 38991726-(Pyrrolidin-1-yl)pyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Combine 5-nitro-2-pyrrolidin-1-yl-pyridine (5.6 g, 29 mmol), palladium hydroxide (1.96 g, 35 wt. %), ammonium formate (9.1 g, 145 mmol), 1N HCl/Et2O (41 ml), in methanol (289 ml) and stir. Heat reaction mixture to reflux for 1 hour. Cool reaction mixture and add carbon to decolorize. Filter the solution through celite, add 50 ml of saturated NaHCO3, and evaporate in vacuo to remove the methanol and ether. Extract the residue 3 times into CH2Cl2 from saturated NaHCO3, dry over Na2SO4, and evaporate in vacuo to obtain 6-pyrrolidin-1-yl-pyridin-3-ylamine. Mass spec.: M+1=164 (AP+).

Aufarbeitung

  1. temperatureHeat
  2. customreaction mixture
  3. temperatureto reflux for 1 hour
  4. temperatureCool
  5. customreaction mixture
  6. additionadd carbon
  7. filtrationFilter the solution through celite
  8. additionadd 50 ml of saturated NaHCO3
  9. customevaporate in vacuo
  10. customto remove the methanol and ether
  11. extractionExtract the residue 3 times into CH2Cl2 from saturated NaHCO3
  12. dry with materialdry over Na2SO4
  13. customevaporate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0ab3b78f69d34acba908fdf85c00aa0c
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566367B2

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