N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide → 7-methoxy-8-nitroisoquinolin-1(2H)-one

HRID 577487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577487
C(O[CH:4](OCC)[CH2:5][NH:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[N+:16]([O-:18])=[O:17])C>S(=O)(=O)(O)O>[CH3:15][O:14][C:10]1[C:9]([N+:16]([O-:18])=[O:17])=[C:8]2[C:13]([CH:4]=[CH:5][NH:6][C:7]2=[O:19])=[CH:12][CH:11]=1

Komponenten

3

Edukt 1

HCID 86723712N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide

Produkt 1

HCID 867237137-methoxy-8-nitroisoquinolin-1(2H)-oneAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide (296a, 92 g, 0.295 mol) in concentrated sulfuric acid (1 L) was stirred at 70° C. for three hours. After cooling to room temperature, the mixture was slowly poured into ice water (3 L), causing a solid precipitate to form. The precipitate was collected by filtration. The filter cake was washed with water (1 L) and dried to yield 7-methoxy-8-nitroisoquinolin-1(2H)-one (296b, 60 g, 92% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 7.92-7.89 (d, J=9.2 Hz, 1H), 7.81-7.79 (d, J=9.2 Hz, 1H), 7.18-7.15 (t, J=6.6 Hz, 1H), 6.66-6.64 (d, J=7.2 Hz, 1H), 3.95 (s, 3H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customto form
  3. filtrationThe precipitate was collected by filtration
  4. washThe filter cake was washed with water (1 L)
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-92f63782e292472aa0bb5b440c2aa432
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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