Ammonium Hydroxide → 5-(Aminomethyl)pyridin-2-amine

HRID 130670

Reaktionsgleichung

Reaktionsgleichung von HRID 130670
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.B.C1COCC1.[NH4+].[OH-]>Cl>[NH2:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([NH2:1])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 14923Ammonium HydroxideHCID 8182602-Amino-5-cyanopyridineHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 157667715-(Aminomethyl)pyridin-2-amineAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To a solution of 6-aminonicotinonitrile 117-A (5.0 g, 42 mmol) was added a solution of 1 M BH3-THF (294 mL, 294 mmol) at 0° C. (prepared as in J.Org. Chem., Vol. 38, No. 5, 1973). The reaction was stirred at room temperature for 1 hour. The reaction mixture was then slowly pored into ice water. 100 mL 4N HCl was added and stirred for 20 min. The solution was basified with NH4OH to pH of about 11, and then concentrated. THF (300mL×2) was added to the mixture followed by addition of solid KOH (excess). The suspension was stirred. The THF layer was collected by filtration and concentrated to give 5-(aminomethyl)pyridin-2-amine 117-B (4.3 g).

Aufarbeitung

  1. customprepared as in J.Org
  2. stirringstirred for 20 min
  3. concentrationconcentrated
  4. additionTHF (300mL×2) was added to the mixture
  5. additionfollowed by addition of solid KOH (excess)
  6. stirringThe suspension was stirred
  7. filtrationThe THF layer was collected by filtration
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dc84e24aea9d480893515ad0ec3b381a
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381824B2

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