2-Amino-4-nitrobenzonitrile → 2-(Aminomethyl)-5-nitroaniline

HRID 1041791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1041791
CSC.B.[NH2:5][C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]>C1COCC1>[NH2:9][CH2:8][C:7]1[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:6]=1[NH2:5]

Komponenten

4

Edukt 2

HCID 111478972-Amino-4-nitrobenzonitrileHCID 12423031(Dimethyl sulfide)trihydroboron

Produkt 1

HCID 578538082-(Aminomethyl)-5-nitroanilineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Borane-dimethyl sulfide (40 mL, 80 mmol) was added dropwise to a stirring solution of 2-amino-4-nitro-benzonitrile (2.27 g, 14 mmol) in dry THF (50 mL) at room temperature. The mixture was stirred at same temperature for 3 hours, and then carefully quenched with 1N aqueous HCl. The mixture was made basic (pH>11) with 4N sodium hydroxide and extracted with methylene chloride. The organic phase was dried over sodium sulfate, filtered and concentrated to provide 1.75 g of 2-aminomethyl-5-nitro-phenylamine (75%): 1H NMR (300 MHz, CDCl3) δ7.6 (m, 2H), 7.25 (d, 1H), 5.1 (br, 2H), 4.1 (s, 3H); MS (m/e): 168.1 (M+1).

Aufarbeitung

  1. customcarefully quenched with 1N aqueous HCl
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dc2f158842ce40ff89ae6191a283a885
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552186B2

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