4-(4-Nitrobenzyl)pyridine → 4-[(Pyridin-4-yl)methyl]aniline

HRID 1860466

Reaktionsgleichung

Reaktionsgleichung von HRID 1860466
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[N:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:7]2[CH:15]=[CH:16][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:10][CH:11]=1

Komponenten

4

Edukt 1

HCID 141294-(4-Nitrobenzyl)pyridine

Produkt 1

HCID 3071584-[(Pyridin-4-yl)methyl]anilineAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4-(4-nitro-benzyl)-pyridine (24 mmol, 5.1 g) in MeOH (15 mL) was hydrogenated in the presence of 500 mg palladium (10% on activated carbon). After stirring at r.t. for 20 h the reaction mixture was filtered through Celite 521. The filter aid was washed with MeOH several times. The filtrate was evaporated to dryness to afford 4-pyridin-4-ylmethyl-phenylamine (1.84 g) as a grey solid. Anal. RP-HPLC indicated a single product. A solution of this product in MeOH (15 mL) was cooled on an ice bath and was treated first with HCl (conc. 1.75 mL) followed by addition of cyanamide (50% aq soln.; 5 mL). The reaction mixture was heated at reflux for 18 h. The solvent was evaporated and the residue was washed with EtOAc/MeOH (2:1, v/v) to afford N-(4-pyridin-4-ylmethyl-phenyl)-guanidine hydrochloride (2.25 g) as a white solid.

Aufarbeitung

  1. filtrationwas filtered through Celite 521
  2. washThe filter aid was washed with MeOH several times
  3. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1b0b705154734a09a7a0cdd002b584a5
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531479B2

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