4-[(3-Hydroxypropyl)amino]-3-nitrobenzonitrile → 3-Amino-4-((3-hydroxypropyl)amino)benzonitrile

HRID 590407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590407
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[N+:14]([O-])=O>CCO>[NH2:14][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:6]=1[NH:5][CH2:4][CH2:3][CH2:2][OH:1])[C:10]#[N:11]

Komponenten

3

Edukt 1

HCID 223493164-[(3-Hydroxypropyl)amino]-3-nitrobenzonitrile2×

Produkt 1

HCID 223492773-Amino-4-((3-hydroxypropyl)amino)benzonitrileAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 4-[(3-hydroxypropyl)amino]-3-nitrobenzonitrile (Intermediate 95, 13.4 g, 0.06 mol) in EtOH (500 mL) was added, under argon atmosphere, palladium over carbon (350 mg, 3.3 mmol of a 10% Pd/C) and the mixture was degassed. Then, H2 was added up to an internal pressure of 20 psi, and the final suspension was stirred at room temperature for 2.5 hours. The crude was filtered through a Whatmann glass micro fibre filter and the solvent was removed under reduced pressure to afford the title compound as a brownish solid (11.5 g, 95% yield) which was used in the next step without further purification.

Aufarbeitung

  1. additionwas added, under argon atmosphere
  2. custompalladium over carbon (350 mg, 3.3 mmol of a 10% Pd/C) and the mixture was degassed
  3. additionThen, H2 was added up to an internal pressure of 20 psi
  4. filtrationThe crude was filtered through a Whatmann glass micro fibre
  5. filtrationfilter
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2dc2b9ecc0384d7f9da2111b2f260d93
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233108B2

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