Hydrazine hydrate (1:1) → 6-(Aminomethyl)quinoline

HRID 1959621

Reaktionsgleichung

Reaktionsgleichung von HRID 1959621
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.NN>CO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][NH2:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 230792942-(Quinolin-6-ylmethyl)isoindoline-1,3-dione

Produkt 1

HCID 15143846-(Aminomethyl)quinolineAusbeute 45,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(quinolin-6-ylmethyl)isoindoline-1,3-dione (20 g, 69.4 mmol) in MeOH (100 mL) was added hydrazine monohydrate (3.47 g, 69.4 mmol). The solution was heated at reflux for 3 h, then cooled to it and filtered through celite. The filtrate was concentrated in vacuo. EtOAc then was added to the residue and the resulting solution was filtered and concentrated in vacuo to afford 5 g (41%) of the title compound. LCMS (method B): [MH]+=159, tR=0.93 min.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 h
  3. temperaturecooled to it
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionEtOAc then was added to the residue
  7. filtrationthe resulting solution was filtered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c865c1b7f82a4090a42af7ae1a6e6f9d
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410264B2

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