Borane → 2-(Aminomethyl)-4-nitroaniline hydrochloride

HRID 2243096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2243096
B.[NH2:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]=1[C:5]#[N:6].C(O)C.[ClH:17]>C1COCC1>[ClH:17].[NH2:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]=1[CH2:5][NH2:6]

Komponenten

5

Edukt 3

HCID 6331BoraneHCID 285322-Amino-5-nitrobenzonitrileHCID 21887872Ethanol hydrochloride

Produkt 1

HCID 230857072-(Aminomethyl)-4-nitroaniline hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Borane in THF (400 ml, 0.40 mol) is added dropwise to 2-amino-5-nitrobenzonitrile (60 g, 0.35 mol) in THF (600 ml) at 0° C. The mixture is allowed to warm to room temperature and is stirred for 16 hours. The resulting mixture is cooled to 0° C. and 200 ml of absolute ethanol/HCl are added. The THF is removed and the product is filtered off and recrystallized from isopropyl ether. Yield: 68.8 g (96%); Rf (1:1 methanol/chloroform): 0.15; IR (KBr): 3416, 2980, 1669, 1601, 1474, 1285 cm−1.

Aufarbeitung

  1. temperatureThe resulting mixture is cooled to 0° C.
  2. customThe THF is removed
  3. filtrationthe product is filtered off
  4. customrecrystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2daf6468f51d4088bec0ba1fb58295f7
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674809B2

Notizen zur Reaktion

Wird geladen…