Ammonia → HCID 16100402, Verbindung

HRID 1961683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1961683
[C:1]([CH2:3][C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[C:5]=1[CH2:13][C:14]#[N:15])#N.N>C(O)C.[Ni]>[O:10]1[C:6]2[C:5]3[CH2:13][CH2:14][NH:15][CH2:1][CH2:3][C:4]=3[CH:12]=[CH:11][C:7]=2[O:8][CH2:9]1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 161004012,2'-(2H-1,3-Benzodioxole-4,5-diyl)diacetonitrile

Produkt 1

HCID 16100402HCID 16100402, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

(5-Cyanomethyl-1,3-benzodioxol-4-yl)acetonitrile (6.00 g, 30.0 mmoles) from Example 58C was reductively cyclized with Raney-Nickel (1.21 g) under a hydrogen atmosphere and high pressure (1100 p.s.i.) in a 10% ammonia in ethanol solution (121 mL) at 100° C. for one hour. The mixture was cooled, and the catalyst filtered off and washed with hot ethanol. The mixture was concentrated under reduced pressure, and the residue purified by normal phase HPLC on a Biotage pre-packed silica gel column eluting with 7:3 methylene chloride:methanol to afford the title compound. MS (DCI) m/z 192 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationthe catalyst filtered off
  3. washwashed with hot ethanol
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue purified by normal phase HPLC on a Biotage pre-packed silica gel column
  6. washeluting with 7:3 methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-f5138eb610c44e29ade3ff04d26ab9b5
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415354B2

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