Acetohydrazide → 7-Bromo-8-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

HRID 1521640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521640
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[NH:8][C:7](=S)[CH2:6][CH2:5]2.[C:14]([NH:17][NH2:18])(=O)[CH3:15]>C(O)CCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]1[C:14]([CH3:15])=[N:17][N:18]=[C:7]1[CH2:6][CH2:5]2

Komponenten

4

Edukt 2

HCID 14039AcetohydrazideHCID 891560686-bromo-7-fluoro-3,4-dihydroquinoline-2(1H)-thione

Produkt 1

HCID 709774737-Bromo-8-fluoro-1-methyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a stirred solution of 6-bromo-7-fluoro-3,4-dihydroquinoline-2(1H)-thione (122-4; 7.0 g, 0.026 mol) in n-butanol (30 mL) was added acetic hydrazide (4.81 g, 0.065 mol). Reaction mass was warmed at 120° C. for 16 h. The reaction mixture was concentrated and directly purified by silica gel column chromatography to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.88-7.86 (d, J=7.6 Hz, 1H), 7.70-7.67 (d, J=10 Hz, 1H), 3.0-2.94 (m, 4H), 2.67 (s, 3H). MS (M+1): 284.2.

Aufarbeitung

  1. customReaction mass
  2. concentrationThe reaction mixture was concentrated
  3. customdirectly purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7249d9a178184b75b1b918eb68869e87
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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